Benzene → HCID 22800117, compound

HRID 1439190Notes

Reaction equation

HRID 1439190 reaction equation
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C:11](=[C:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH:10]=[CH:9][C:8]1=[CH:7][C:6](=[O:22])[CH2:5][CH2:4]2.[BH4-].[Na+].C1C=CC=CC=1>CO>[OH:22][C@H:6]1[CH2:5][CH2:4][C@@:3]2([CH2:2][OH:1])[C:8]([CH:9]=[CH:10][C:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C:12]=3[CH2:13][CH2:14][C@@H:15]2[OH:21])=[CH:7]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 4311764Sodium borohydrideHCID 54385918HCID 54385918, compound

Product 1

HCID 22800117HCID 22800117, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 4.5 g of 19-hydroxyandrost-4,6,8(14)-trien-3,17-dione in 40 ml of methanol, which was cooled externally by an ice-bath, was added 1.8 g of sodium borohydride with stirring. Stirring was continued for 1 hour, 450 ml of benzene was added and the mixture was concentrated at reduced pressure to a small volume. Benzene and a small volume of water was added and the mixture was concentrated again. Subsequent filtration and recrystallization of the precipitate from methanol gave 3β,17β,19-trihydroxyandrosta-4,6,8(14)-triene as a white solid, uv max 275 (sh), 285 and 298 (sh) mμ.

Workup

  1. temperaturewas cooled externally by an ice-bath
  2. stirringStirring
  3. concentrationthe mixture was concentrated at reduced pressure to a small volume
  4. additionBenzene and a small volume of water was added
  5. concentrationthe mixture was concentrated again
  6. filtrationSubsequent filtration and recrystallization of the precipitate from methanol

Sources & evidence

ORD record
ord-d149996e61b245149a4a9bcdea82c7eb
Source dataset
uspto-grants-1977_11
Patent number
US04058539

Reaction notes

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