Potassium Hydroxide → HCID 69964716, compound

HRID 650356Notes

Reaction equation

HRID 650356 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-7bcf7737226f4b049016de3aeddc78b7
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

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