Toluene → Cholest-4-en-3-one

HRID 866515Notes

Reaction equation

HRID 866515 reaction equation
[OH:1][C@H:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:19])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:3]1.C1(C)C=CC=CC=1.C1CCCCC1.CC([O-])C.CC([O-])C.CC([O-])C.[Al+3]>CCOCC>[CH3:18][CH:16]([CH2:15][CH2:14][CH2:13][C@H:12]([C@@H:11]1[C@:20]2([CH3:28])[C@H:8]([C@H:7]3[C@H:23]([CH2:22][CH2:21]2)[C@:24]2([CH3:27])[C:4](=[CH:3][C:2](=[O:1])[CH2:26][CH2:25]2)[CH2:5][CH2:6]3)[CH2:9][CH2:10]1)[CH3:19])[CH3:17]

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 5997CholesterolHCID 8078CyclohexaneHCID 11143Aluminum isopropoxide

Product 1

HCID 91477Cholest-4-en-3-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

111 g. of 3β-hydroxy-5-cholestene is heated in 2.2 l. of toluene and 111 ml. of cyclohexane to boiling. A solution of 55.5 g. of aluminum isopropylate in 666 ml. of toluene is added dropwise thereto. The mixture is then further heated for 90 minutes with gradual distillation. The cooled reaction solution is diluted with ether, washed with dilute sulfuric acid and water, and concentrated. The residue is distilled with steam and the crude product, obtained after extraction with methylene chloride, is chromatographed on silica gel. After recrystallization from methanol, 70 g. of 4-cholesten-3-one is obtained, m.p. 79° - 80.5° C.

Workup

  1. temperatureThe mixture is then further heated for 90 minutes with gradual distillation
  2. customThe cooled reaction solution
  3. washwashed with dilute sulfuric acid and water
  4. concentrationconcentrated
  5. distillationThe residue is distilled with steam
  6. customthe crude product, obtained
  7. extractionafter extraction with methylene chloride
  8. customis chromatographed on silica gel
  9. customAfter recrystallization from methanol, 70 g

Sources & evidence

ORD record
ord-3ae943e8573c47a38c4ad419ccde1980
Source dataset
uspto-grants-1978_07
Patent number
US04100026

Reaction notes

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