Reaction #2153

ord-dda6f0d331b14af09fea8960240ce219

Reaction equation

C#CCOC1CCCCO1
2-(2-propinyloxy)tetrahydro-2H-pyrane
[Li][CH2]CCC
butyllithium
→
C[C@]12CC[C@H]3[C@@H](CCC4=CCCC[C@@H]43)[C@@H]1CC[C@@H]2O
7G
C[C@]12CC[C@H]3[C@@H](CCC4=CCCC[C@@H]43)[C@@H]1CC[C@@H]2O
4-estren-17β-ol

Reactants

—
solution
C#CCOC1CCCCO1
2-(2-propinyloxy)tetrahydro-2H-pyrane
[Li][CH2]CCC
butyllithium
—
3D

Reagents

None

Solvents

CCCCCC
hexane
C1CCOC1
tetrahydrofuran

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

As described under 3D, 460 mg of 7G is produced from 442 mg of 7F with 1.30 ml of 2-(2-propinyloxy)tetrahydro-2H-pyrane and 5.36 ml of a 15% solution of butyllithium in hexane in 70 ml of tetrahydrofuran.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05728689uspto-grants-1998_03