Water → HCID 13061706, compound

HRID 2199015Notes

Reaction equation

HRID 2199015 reaction equation
[CH3:1][C@@:2]12[C@H:11]3[CH2:12][CH2:13][C@:14]4([CH3:20])[C:18](=O)[CH2:17][CH2:16][C@H:15]4[C@@H:10]3[C@H:9](O)C[C@H:7]1[CH2:6][C@H:5]([OH:22])[CH2:4][CH2:3]2.C[C:24]([CH3:27])([O-:26])[CH3:25].[K+].O>O1CCCC1.[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C>[CH3:9]/[CH:10]=[C:15]1/[CH2:16][CH2:17][C@@H:18]2[C@:14]/1([CH3:20])[CH2:13][CH2:12][C@H:11]1[C@H:25]2[C@H:24]([OH:26])[CH2:27][C@H:7]2[C@:2]1([CH3:1])[CH2:3][CH2:4][C@@H:5]([OH:22])[CH2:6]2

Participants

6

Reactant 3

HCID 962WaterHCID 2112314121080-62-6HCID 23665647Potassium tert-butoxide

Product 1

HCID 13061706HCID 13061706, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.282 g (ca. 0.0034 mol) of 3α,5β,7α-3,7-dihydroxyandrostan-17-one in 5 ml of tetrahydrofuran was added to a room temperature solution of 113 ml of tetrahydrofuran, 1.875 g (0.0167 mol) of potassium t-butoxide and 6.215 g (0.0167 mol) of ethyltriphenylphosphonium bromide. The mixture was stirred under argon for 72 hr. and then was poured into 750 ml of water containing 250 g of ice. After 30 min., the mixture was collected by suction filtration and washed with water. The dried, crude material (3.0 g) was chromatographed on 200 g of silica gel to afford, on elution with ethyl acetate--hexane (2:1), 0.888 g of material (82%). Trace amounts of impurities were removed by dissolving in a mixture of hexane and methylene chloride. The methylene chloride was distilled, the mixture was cooled, and the solid product, (Z)-3α,5β,7α-pregn-17(20)-ene-3,7-diol, was collected by filtration. The analytical sample was recrystallized from ethyl acetate then acetonitrile, mp 160°-161° C.

Workup

  1. waitAfter 30 min.
  2. filtrationthe mixture was collected by suction filtration
  3. washwashed with water
  4. customThe dried, crude material (3.0 g) was chromatographed on 200 g of silica gel

Sources & evidence

ORD record
ord-8103597c91334978b7b38d1ee22b349a
Source dataset
uspto-grants-1982_11
Patent number
US04360470

Reaction notes

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