Potassium Hydroxide → HCID 69964716, compound

HRID 361666Notes

Reaction equation

HRID 361666 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[CH2:27][C:26]2[CH:25]=[C:24]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:23]=[CH:22][C:21]=2[C@@H:20]2[C@@H:11]1[C:12]1[C@@:16]([CH2:18][CH2:19]2)([CH3:17])[C@@H:15]([OH:36])[CH2:14][CH:13]=1)(=O)C.[OH-].[K+]>ClCCl>[CH2:29]([O:28][C:24]1[CH:23]=[CH:22][C:21]2[C@@H:20]3[C@H:11]([C:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C@@H:15]([OH:36])[CH2:14][CH:13]=4)[C@H:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][OH:4])[CH2:27][C:26]=2[CH:25]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 69965370HCID 69965370, compound

Product 1

HCID 69964716HCID 69964716, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.16 g of 7α-(5-acetoxypentyl)-3-benzyloxy-estra-1,3,5(10),14-tetraen-17β-ol is saponified with 38 ml of 1N methanolic potassium hydroxide solution overnight at room temperature. The reaction mixture is poured into ice-cold saturated common salt solution, the precipitate is suctioned off, taken up in dichloromethane, washed with saturated common salt solution, dried on sodium sulfate and concentrated by evaporation. 1.86 g of 3-benzyloxy-7α-(5-hydroxypentyl)-estra-1,3,5(10),14-tetraen-17β-ol is obtained as foam.

Workup

  1. additionThe reaction mixture is poured into ice-cold saturated common salt solution
  2. washwashed with saturated common salt solution
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-3ef38600bf104137a1163b23f84616ee
Source dataset
uspto-grants-1999_02
Patent number
US05866560

Reaction notes

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