Acetic Acid → HCID 68145322, compound

HRID 1414982Notes

Reaction equation

HRID 1414982 reaction equation
[CH2:1]([C@:17]12[CH2:25][CH2:24][C:23]3[C:26]4[CH:27]=[CH:28][C:29]([O:34][CH3:35])=[CH:30][C:31]=4[CH2:32][CH2:33][C:22]=3[C@@H:21]1[CH2:20][CH2:19][C:18]2=[O:36])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[BH4-].[Na+].C(O)(=O)C>C(O)C>[CH2:1]([C@:17]12[CH2:25][CH2:24][C:23]3[C:26]4[CH:27]=[CH:28][C:29]([O:34][CH3:35])=[CH:30][C:31]=4[CH2:32][CH2:33][C:22]=3[C@@H:21]1[CH2:20][CH2:19][C@@H:18]2[OH:36])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 54354713HCID 54354713, compound

Product 1

HCID 68145322HCID 68145322, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Stir a solution of 13β-cetyl-3-methoxygona-1,3,5(10),8-tetraen-17-one (0.60 g.) and sodium borohydride (0.20 g.) in ethanol (110cc.) for 2 hours and leave overnight. Reflux with stirring for 2 hours, cool, and add an excess of 50% aqueous acetic acid. Evaporate the mixture to dryness under reduced pressure and partition the residue between ether and water. Work up in the usual manner to get an ether solution of the title product as a gum; infrared absorption peak at 3.37 μ (hydroxyl) with no band in the 5.71-5.88 mμ region; ultraviolet absorption peak at 278 mμ.

Workup

  1. customleave overnight
  2. temperatureReflux
  3. temperaturecool
  4. customEvaporate the mixture to dryness under reduced pressure
  5. custompartition the residue between ether and water

Sources & evidence

ORD record
ord-00ec21df7bde4bef854bbf1d9a7fc154
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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