Hydrochloric Acid → HCID 57277431, compound

HRID 1603351Notes

Reaction equation

HRID 1603351 reaction equation
C(OCCCCC[CH:10]([O:17][C:18]1[CH:35]=[CH:34][C:33]2[C@@H:32]3[C@H:23]([C@H:24]4[C@@:28]([CH2:30][CH2:31]3)([CH3:29])[C:27](=[O:36])[CH2:26][CH2:25]4)[CH2:22][CH2:21][C:20]=2[CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)C.[OH-].[Na+].Cl.C([O:43][CH2:44][CH3:45])(=O)C.O1C[CH2:49][CH2:48][CH2:47]1>CO>[CH2:10]([O:17][C:18]1[CH:35]=[CH:34][C:33]2[C@@H:32]3[C@H:23]([C@H:24]4[C@@:28]([CH2:30][CH2:31]3)([CH3:29])[C:27](=[O:36])[CH2:26][CH2:25]4)[C@H:22]([CH2:47][CH2:48][CH2:49][CH2:45][CH2:44][OH:43])[CH2:21][C:20]=2[CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 22941812HCID 22941812, compound

Product 1

HCID 57277431HCID 57277431, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7.26 g of α-(5-acetoxypentyl)-3-benzyloxy-estra-1,3,5(10)-trien-17-one in 80 ml of methanol and 3 ml of tetrahydrofuran is saponified with 22.2 ml of 2N sodium hydroxide solution overnight at room temperature. The reaction solution is poured into 2N hydrochloric acid, shaken out with ethyl acetate, the organic phase is washed with saturated common salt solution, dried on sodium sulfate and concentrated by evaporation. 6.7 g of 3-benzyloxy-7α-(5-hydroxypentyl)-estra-1,3,5(10)-trien-17-one is obtained as foam.

Workup

  1. washthe organic phase is washed with saturated common salt solution
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-f6367eeb6d1f4135ad1492360ba609f6
Source dataset
uspto-grants-1999_11
Patent number
US05986115

Reaction notes

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