Acetic Acid → HCID 86738323, compound

HRID 2059302Notes

Reaction equation

HRID 2059302 reaction equation
[CH2:1]([C@@:4]12[C@@H:21]3[C@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:22])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]1=[CH:8][C:7](=[O:23])[CH2:6][CH2:5]2)[C:2]#[CH:3].[BH4-].[K+].C(O)(=O)C>CO>[OH:22][C@H:16]1[CH2:15][CH2:14][C@H:13]2[C@H:12]3[C@H:21]([CH2:20][CH2:19][C@:17]12[CH3:18])[C@:4]1([CH2:1][C:2]#[CH:3])[C:9](=[CH:8][C:7](=[O:23])[CH2:6][CH2:5]1)[CH2:10][CH2:11]3

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4192641Potassium borohydrideHCID 9904788Plomestane

Product 1

HCID 86738323HCID 86738323, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 312 mg of 10-(2-propynyl)estr-4-ene-3,17-dione in 10 ml of absolute methanol is treated with 15 mg of potassium borohydride at 0° C. for 1 hour. Acetic acid (0.05 ml) is added and the solvent is evaporated. The residue is dissolved in ether, the ether solution is washed with 1 N hydrochloric acid and with brine and dried, and the solvent is evaporated. The residue is recrystallized from methanol to give 17β-hydroxy-10-(2-propynyl)estr-4-en-3-one. This compound has the following structural formula ##STR9##

Workup

  1. customthe solvent is evaporated
  2. dissolutionThe residue is dissolved in ether
  3. washthe ether solution is washed with 1 N hydrochloric acid and with brine
  4. customdried
  5. customthe solvent is evaporated
  6. customThe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-0af9b10ef6d54de9a42a61a009ab3a98
Source dataset
uspto-grants-1982_03
Patent number
US04322416

Reaction notes

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