Acetic Acid → HCID 18600625, compound

HRID 637620Notes

Reaction equation

HRID 637620 reaction equation
[BH4-].[Na+].[F:3][CH:4]([F:25])[C@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][C:19]2=[O:23])[C@H:15]2[C@H:6]1[C@@H:7]1[C:12]([CH2:13][CH2:14]2)=[CH:11][C:10](=[O:24])[CH2:9][CH2:8]1.[BH4-].C(O)(=O)C>C1COCC1.O>[F:3][CH:4]([F:25])[C@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][C@@H:19]2[OH:23])[C@H:15]2[C@H:6]1[C@@H:7]1[C:12]([CH2:13][CH2:14]2)=[CH:11][C:10](=[O:24])[CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 28123BorohydrideHCID 4311764Sodium borohydrideHCID 57236774HCID 57236774, compound

Product 1

HCID 18600625HCID 18600625, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A sodium borohydride solution (100 mg in 50 ml absolute ethanol, 4 ml) is added to a solution of 11β-difluoromethyl-estr-4-ene-3,17-dione (II, Example 2, 20 mg) in THF (4 ml) with cooling. After 1 hr another 1 ml of the borohydride solution is added. After 15 minutes acetic acid in water (5%, 10 ml) is added. Most of the solvent is removed under reduced pressure and the product extracted with diethyl ether. The product is chromatographed thru silica gel eluting with ethyl acetate/hexane (60/40). The appropriate fractions are pooled and concentrated to give the title compound, NMR (CDCl3) 0.81, 3.63, 5.84, 6.05 and 55.5 δ.

Workup

  1. temperaturewith cooling
  2. customMost of the solvent is removed under reduced pressure
  3. extractionthe product extracted with diethyl ether
  4. customThe product is chromatographed
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8bb899c793374e2eaa27245d4befd2e8
Source dataset
uspto-grants-1985_12
Patent number
US04557867

Reaction notes

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