Sodium borohydride → HCID 68143930, compound

HRID 1077163Notes

Reaction equation

HRID 1077163 reaction equation
[CH2:1]([C@:4]12[CH2:12][CH2:11][C:10]3[C:13]4[CH:14]=[CH:15][C:16]([O:21][CH3:22])=[CH:17][C:18]=4[CH2:19][CH2:20][C:9]=3[C@@H:8]1[CH2:7][CH2:6][C:5]2=[O:23])[CH2:2][CH3:3].[BH4-].[Na+]>CO>[CH2:1]([C@:4]12[CH2:12][CH2:11][C:10]3[C:13]4[CH:14]=[CH:15][C:16]([O:21][CH3:22])=[CH:17][C:18]=4[CH2:19][CH2:20][C:9]=3[C@@H:8]1[CH2:7][CH2:6][C@@H:5]2[OH:23])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 54182015(±)-3-Methoxy-13-propylgona-1,3,5(10),8-tetraen-17-one

Product 1

HCID 68143930HCID 68143930, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 13β-propyl-3-methoxygona-1,3,5(10),8-tetraen-17-one (3.5 g.) to a solution of sodium borohydride (1.16 g.) in methanol (120 cc.). Heat the reaction mixture to reflux with stirring for 30 minutes. Concentrate the resulting solution, adjust its pH to 6 with aqueous acetic acid and filter off the resulting white precipitate which is the title product, (3.1 g.), m.p. 134°-8°; ultra-violet absorption peak at 278 mμ (ε15,350); infrared showed a band due to hydroxyl but no ketone present.

Workup

  1. temperatureHeat the reaction mixture
  2. temperatureto reflux
  3. concentrationConcentrate the resulting solution
  4. filtrationfilter off the resulting white precipitate which

Sources & evidence

ORD record
ord-3c5969ae87314b1c84ef31762a4adb85
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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