Hydrochloric Acid → HCID 12876731, compound

HRID 1156040Notes

Reaction equation

HRID 1156040 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C:12](=[O:21])[C@H:11]([CH3:22])[CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.[BH4-].[Na+].Cl.O>C(O)C>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@@H:12]([OH:21])[C@H:11]([CH3:22])[CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 12876725HCID 12876725, compound

Product 1

HCID 12876731HCID 12876731, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

16.0 g of 3-methoxy-16α-methyl-1,3,5(10)-estratrien-17-one is dissolved in 200 ml of ethanol and, under ice cooling, combined dropwise with a solution of 2.1 g of sodium borohydride in 100 ml of 80% aqueous ethanol. The mixture is stirred for 16 hours at room temperature, then 1 N hydrochloric acid is gently added to the reaction solution, the latter is poured into water and extracted with ethyl acetate. Crystallization from acetonitrile yields 13.4 g of 3-methoxy-16α-methyl-1,3,5(10)-estratrien-17β-ol, m.p. 100°-102° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customCrystallization from acetonitrile

Sources & evidence

ORD record
ord-b4457fb835ca4d48990ac3dc872acbd8
Source dataset
uspto-grants-1982_06
Patent number
US04333928

Reaction notes

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