Sulfuric Acid → HCID 70048666, compound

HRID 725182Notes

Reaction equation

HRID 725182 reaction equation
C[O:2][C:3](/[CH:5]=[CH:6]/[C@@H:7]1[C@:15]2([CH3:16])[C@@:10]([OH:31])([CH2:11][C@@H:12]([C:17]3[CH:22]=[CH:21][C:20]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])=[CH:19][CH:18]=3)[CH2:13][CH2:14]2)[CH2:9][CH2:8]1)=O.CC(C[AlH]CC(C)C)C.OS(O)(=O)=O>C1COCC1>[OH:2][CH2:3]/[CH:5]=[CH:6]/[C@@H:7]1[C@:15]2([CH3:16])[C@@:10]([OH:31])([CH2:11][C@@H:12]([C:17]3[CH:22]=[CH:21][C:20]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:25])[CH3:26])=[CH:19][CH:18]=3)[CH2:13][CH2:14]2)[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14487Diisobutylaluminum hydrideHCID 88124873HCID 88124873, compound

Product 1

HCID 70048666HCID 70048666, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 3.90 g of (1R,3aS,5S,7aR)-1-[(E)-2-methoxycarbonyl-1-ethenyl]-5-(4-tert-butyl-dimethylsilyloxyphenyl)-7a-methylperhydroinden-3a-ol in 50 ml of anhydrous THF, cooled at -78° C., 45 ml of 1N DIBAH in THF were added and the mixture was stirred at -78° C. for 1 hr, then at room temperature for 8 hrs. The reaction mixture was cooled to 0° C. and 100 ml of 1N H2SO4 were cautiously added and stirring was continued at room temperature for 1 hr. The mixture was then extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure. The residue was purified by flash chromatography (SiO2) with n-hexane/ethyl acetate 7:3 as the eluant to give 2.95 g of (1R,3aS,5S,7aR)-1-[(E)-3-hydroxy-1-propenyl]-5-(4-tert-butyldimethylsilyloxyphenyl)-7a-methylperhydroinden-3a-ol as a white solid.

Workup

  1. waitat room temperature for 8 hrs
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. stirringstirring
  4. waitwas continued at room temperature for 1 hr
  5. extractionThe mixture was then extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customevaporated to dryness under reduced pressure
  8. customThe residue was purified by flash chromatography (SiO2) with n-hexane/ethyl acetate 7:3 as the eluant

Sources & evidence

ORD record
ord-fcdc6132e51e473593dfbff6a51ef768
Source dataset
uspto-grants-1998_01
Patent number
US05705531

Reaction notes

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