diff --git a/gcc/config/i386/i386.md b/gcc/config/i386/i386.md
index f90cf1ca7341c637b02b3cd17634c7e6d03b00b0..abaf2f311e89458617d70bac0f54ef660dc1e0f8 100644
--- a/gcc/config/i386/i386.md
+++ b/gcc/config/i386/i386.md
@@ -3414,6 +3414,21 @@
   [(set_attr "type" "imovx")
    (set_attr "mode" "SI")])
 
+;; Split sign-extension of single least significant bit as and x,$1;neg x
+(define_insn_and_split "*extv<mode>_1_0"
+  [(set (match_operand:SWI48 0 "register_operand" "=r")
+	(sign_extract:SWI48 (match_operand:SWI48 1 "register_operand" "0")
+			    (const_int 1)
+			    (const_int 0)))
+   (clobber (reg:CC FLAGS_REG))]
+  ""
+  "#"
+  ""
+  [(parallel [(set (match_dup 0) (and:SWI48 (match_dup 1) (const_int 1)))
+	      (clobber (reg:CC FLAGS_REG))])
+   (parallel [(set (match_dup 0) (neg:SWI48 (match_dup 0)))
+	      (clobber (reg:CC FLAGS_REG))])])
+
 (define_expand "extzv<mode>"
   [(set (match_operand:SWI248 0 "register_operand")
 	(zero_extract:SWI248 (match_operand:SWI248 1 "register_operand")
diff --git a/gcc/testsuite/gcc.target/i386/pr106245-2.c b/gcc/testsuite/gcc.target/i386/pr106245-2.c
new file mode 100644
index 0000000000000000000000000000000000000000..47b0d27c0483b498dcd362986bdae1f9f3bda756
--- /dev/null
+++ b/gcc/testsuite/gcc.target/i386/pr106245-2.c
@@ -0,0 +1,10 @@
+/* { dg-do compile } */
+/* { dg-options "-O2" } */
+
+int f(int a)
+{
+    return (a << 31) >> 31;
+}
+
+/* { dg-final { scan-assembler "andl" } } */
+/* { dg-final { scan-assembler "negl" } } */
diff --git a/gcc/testsuite/gcc.target/i386/pr106245-3.c b/gcc/testsuite/gcc.target/i386/pr106245-3.c
new file mode 100644
index 0000000000000000000000000000000000000000..4ec634281ed9d437f554e09fe143248aff48bd63
--- /dev/null
+++ b/gcc/testsuite/gcc.target/i386/pr106245-3.c
@@ -0,0 +1,11 @@
+/* { dg-do compile { target ia32 } } */
+/* { dg-options "-O2" } */
+
+long long f(long long a)
+{
+    return (a << 63) >> 63;
+}
+
+/* { dg-final { scan-assembler "andl" } } */
+/* { dg-final { scan-assembler "negl" } } */
+/* { dg-final { scan-assembler "cltd" } } */
diff --git a/gcc/testsuite/gcc.target/i386/pr106245-4.c b/gcc/testsuite/gcc.target/i386/pr106245-4.c
new file mode 100644
index 0000000000000000000000000000000000000000..ef77ee539b4e562e46049f1064f7c84eaa877c2b
--- /dev/null
+++ b/gcc/testsuite/gcc.target/i386/pr106245-4.c
@@ -0,0 +1,10 @@
+/* { dg-do compile { target { ! ia32 } } } */
+/* { dg-options "-O2" } */
+
+long long f(long long a)
+{
+    return (a << 63) >> 63;
+}
+
+/* { dg-final { scan-assembler "andl" } } */
+/* { dg-final { scan-assembler "negq" } } */
diff --git a/gcc/testsuite/gcc.target/i386/pr106245-5.c b/gcc/testsuite/gcc.target/i386/pr106245-5.c
new file mode 100644
index 0000000000000000000000000000000000000000..0351866c6a7d34cdeb869bc7d68eb54a284eb822
--- /dev/null
+++ b/gcc/testsuite/gcc.target/i386/pr106245-5.c
@@ -0,0 +1,11 @@
+/* { dg-do compile { target int128 } } */
+/* { dg-options "-O2" } */
+
+__int128 f(__int128 a)
+{
+  return (a << 127) >> 127;
+}
+
+/* { dg-final { scan-assembler "andl" } } */
+/* { dg-final { scan-assembler "negq" } } */
+/* { dg-final { scan-assembler "cqto" } } */