Acetic Acid → HCID 56607196, compound

HRID 848026Notes

Reaction equation

HRID 848026 reaction equation
[C:1]([CH2:3][C@@:4]12[C@@H:20]([C:21](=[O:23])[CH3:22])[CH2:19][CH2:18][C@H:17]1[C@H:16]1[C@@H:7]([C@:8]3([CH3:25])[C:13]([CH2:14][CH2:15]1)=[CH:12][C:11](=[O:24])[CH2:10][CH2:9]3)[CH2:6][CH2:5]2)#[CH:2].[BH4-].[Na+].C(O)(=O)C>CO>[C:1]([CH2:3][C@@:4]12[C@@H:20]([CH:21]([OH:23])[CH3:22])[CH2:19][CH2:18][C@H:17]1[C@H:16]1[C@@H:7]([C@:8]3([CH3:25])[C:13]([CH2:14][CH2:15]1)=[CH:12][C:11](=[O:24])[CH2:10][CH2:9]3)[CH2:6][CH2:5]2)#[CH:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 10359794HCID 10359794, compound

Product 1

HCID 56607196HCID 56607196, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4.2 g of 18-ethynylpregn-4-ene-3,20-dione in 125 ml of methanol is cooled to 0° C. and 950 mg of sodium borohydride is added. The resulting mixture is stirred at 0° C. for 1 hour and then allowed to warm to room temperature over an additional hour. Acetic acid is then added and the solution is concentrated. The resulting residue is suspended in ethyl acetate, washed with water, aqueous sodium bicarbonate and brine and dried, and the solvent is evaporated. The residue is dissolved in 400 ml of chloroform, 42 g of activated manganese dioxide is added, and the resulting suspension is stirred for 24 hours. The inorganic solid is then removed by filtration through Celite and the filter cake is washed thoroughly with hot chloroform. The filtrate is then concentrated and the residue is purified by recrystallization from acetone/hexane to give 18-ethynyl-20-hydroxypregn-4-en-3-one.

Workup

  1. temperatureto warm to room temperature over an additional hour
  2. concentrationthe solution is concentrated
  3. washwashed with water, aqueous sodium bicarbonate and brine
  4. customdried
  5. customthe solvent is evaporated
  6. dissolutionThe residue is dissolved in 400 ml of chloroform
  7. addition42 g of activated manganese dioxide is added
  8. stirringthe resulting suspension is stirred for 24 hours
  9. customThe inorganic solid is then removed by filtration through Celite
  10. washthe filter cake is washed thoroughly with hot chloroform
  11. concentrationThe filtrate is then concentrated
  12. customthe residue is purified by recrystallization from acetone/hexane

Sources & evidence

ORD record
ord-db7b4a5cb52846f49b7f636bb4c2dab6
Source dataset
uspto-grants-1981_10
Patent number
US04293548

Reaction notes

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