HCID 57243272, compound → HCID 11742322, compound

HRID 1077441Notes

Reaction equation

HRID 1077441 reaction equation
[CH2:1]([C:3]1(O)[CH:27]=[C:26]2[C@:21]([CH3:29])([CH2:22][CH2:23][C@H:24]([OH:28])[CH2:25]2)[C@@H:20]2[C@@H:4]1[C@H:5]1[C@:17]([CH3:30])([CH2:18][CH2:19]2)[C@@H:8]([C@H:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:7][CH2:6]1)[CH3:2]>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[C@@H:4]2[C@@H:20]([C@:21]3([CH3:29])[C:26]([CH:27]=1)=[CH:25][C:24](=[O:28])[CH2:23][CH2:22]3)[CH2:19][CH2:18][C@@:17]1([CH3:30])[C@H:5]2[CH2:6][CH2:7][C@@H:8]1[C@H:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH3:2]

Participants

3

Reactant 1

HCID 57243272HCID 57243272, compound

Product 1

HCID 11742322HCID 11742322, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The above Grignard product 2, 5.13 g (11.9 mmol) was dissolved in 50 ml toluene and cyclohexanone and about 40 ml of solvent distilled off under vacuum. To this was added 7.2 g aluminum isopropoxide and the reaction mixture refluxed overnight for 15 hours. The mixture was cooled, diluted with ethyl acetate, washed with sodium potassium tartarate, brine, and the organic layer was concentrated under vacuum and the residue steam distilled. The residue was extracted with ethyl acetate, the ethyl acetate layer, washed with brine, dried and purified by column chromatography on silica gel, eluting with 5% EtOAc/hexane to yield the title compound 3. Rf=0.58 (20% EtOAc/hexane). Mass spec: 412(M=1) by FAB, Calc'd. 411.9.

Workup

  1. distillationcyclohexanone and about 40 ml of solvent distilled off under vacuum
  2. additionTo this was added 7.2 g aluminum isopropoxide
  3. temperaturethe reaction mixture refluxed overnight for 15 hours
  4. temperatureThe mixture was cooled
  5. additiondiluted with ethyl acetate
  6. washwashed with sodium potassium tartarate, brine
  7. concentrationthe organic layer was concentrated under vacuum
  8. distillationthe residue steam distilled
  9. extractionThe residue was extracted with ethyl acetate
  10. washthe ethyl acetate layer, washed with brine
  11. customdried
  12. custompurified by column chromatography on silica gel
  13. washeluting with 5% EtOAc/hexane

Sources & evidence

ORD record
ord-ac2ed8992bb748f59fd043de9907f4ef
Source dataset
uspto-grants-1996_08
Patent number
US05543417

Reaction notes

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