Acetic Acid → HCID 22790405, compound

HRID 1077164Notes

Reaction equation

HRID 1077164 reaction equation
[BH4-].[Na+].[CH2:3]([C@:7]12[CH2:15][CH2:14][C:13]3[C:16]4[CH:17]=[CH:18][C:19]([O:24][CH3:25])=[CH:20][C:21]=4[CH2:22][CH2:23][C:12]=3[C@@H:11]1[CH2:10][CH2:9][C:8]2=[O:26])[CH:4]([CH3:6])[CH3:5].C(O)(=O)C>CO>[CH2:3]([C@:7]12[CH2:15][CH2:14][C:13]3[C:16]4[CH:17]=[CH:18][C:19]([O:24][CH3:25])=[CH:20][C:21]=4[CH2:22][CH2:23][C:12]=3[C@@H:11]1[CH2:10][CH2:9][C@@H:8]2[OH:26])[CH:4]([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 53866954HCID 53866954, compound

Product 1

HCID 22790405HCID 22790405, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of sodium borohydride (6.0 g.) in methanol (500 cc. under nitrogen) add 13β-isobutyl-3-methoxygona-1,3,5(10),8-tetraen-17-one (17 g.). Gently heat the reaction mixture for one minute to initiate the reaction and then allow to stand for one hour at room temperature. After adding cautiously glacial acetic acid (20 cc.), concentrate the solution in vacuo to 1/3 of its volume followed by addition of water. Extract the product with ether. Wash the ethereal solution successively with water, sodium bicarbonate, and water, and dry. Evaporate the ether to obtain 13β-isobutyl-3-methoxygona-1,3,5(10),8-tetraen-17β-ol as a gum, (17.0 g.; 99%); ultraviolet absorption peak at 278 mμ (ε14,560).

Workup

  1. temperatureGently heat the reaction mixture for one minute
  2. customthe reaction
  3. concentrationconcentrate the solution in vacuo to 1/3 of its volume
  4. additionfollowed by addition of water
  5. extractionExtract the product with ether
  6. washWash the ethereal solution successively with water, sodium bicarbonate, and water
  7. customdry
  8. customEvaporate the ether

Sources & evidence

ORD record
ord-e68dff39e11749379b34aecf47559a70
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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