Acetic Acid → HCID 86735769, compound

HRID 839520Notes

Reaction equation

HRID 839520 reaction equation
C([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH2:23][O:24]C(=O)C)[C@@H:7]([CH2:8][CH:9]=[C:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@:11]3([OH:35])[CH2:12][CH2:13][C@@H:14]2[O:28]C(=O)C(C)(C)C)[CH2:6]1)(=O)C.[OH-].[K+].C(O)(=O)C.O>C(OCC)(=O)C>[OH:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH2:23][OH:24])[C@@H:7]([CH2:8][CH:9]=[C:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@:11]3([OH:35])[CH2:12][CH2:13][C@@H:14]2[OH:28])[CH2:6]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 22803788HCID 22803788, compound

Product 1

HCID 86735769HCID 86735769, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 20 mg of 3β ,19-diacetoxy-14β-hydroxy-17β-pivaloxy-5α-androst-7-ene and 1.0 ml of 0.2 N methanolic potassium hydroxide was heated under nitrogen at 70° C. for 20 hours whereupon a solution of 0.2 N acetic acid in ethyl acetate was added and the mixture was evaporated. The residue obtained was treated with water and the mixture was then extracted with ethyl acetate. Evaporation of the ethyl acetate solution gave 3β ,14β ,17β ,19-tetrahydroxy-5α-androst-7-ene as indicated by tlc analysis.

Workup

  1. additionwas added
  2. customthe mixture was evaporated
  3. customThe residue obtained
  4. extractionthe mixture was then extracted with ethyl acetate
  5. customEvaporation of the ethyl acetate solution

Sources & evidence

ORD record
ord-5c321744bb2540a989cdc4c4c1f27d5e
Source dataset
uspto-grants-1978_06
Patent number
US04096142

Reaction notes

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