Methanol → HCID 57221674, compound

HRID 1075550Notes

Reaction equation

HRID 1075550 reaction equation
C([O:5][C@H:6]1[CH2:15][CH2:14][CH2:13][C@@H:12]2[C@:7]1([CH3:20])[CH2:8][CH2:9][CH2:10][C@@H:11]2[O:16][C:17](=[O:19])[CH3:18])(C)(C)C.C[Si](I)(C)C.CO>C(Cl)(Cl)(Cl)Cl>[OH:5][C@H:6]1[CH2:15][CH2:14][CH2:13][C@@H:12]2[C@:7]1([CH3:20])[CH2:8][CH2:9][CH2:10][C@@H:11]2[O:16][C:17](=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 18396011HCID 18396011, compound

Product 1

HCID 57221674HCID 57221674, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 4.08 g (14.45 mMol) of acetic acid (1S,4aS,5S,8aR)-5-tert-Butoxy-4a-methyl-decahydronaphtalen-1-yl ester in 7.25 ml of carbon tetrachloride is treated dropwise under stirring and argon atmosphere with 2.56 ml (18.8 mMol) of trimethylsilyliodide by keeping room temperature. After the addition is complete, the reaction mixture is stirred for another 30 minutes, then 1.79 ml of methanol are added and the reaction kept for 15 minutes. The reaction mixture is evaporated in vacuo to dryness to yield 5.52 g. The residue is chromatographed over 500 g of silica gel with hexane/ethylacetate 4/1 to give 2.88 g (88%) of pure acetic acid (1S,4aS,5S,8aR)-5-hydroxy-4a-methyl-decahydronaphtalen-1-yl ester.

Workup

  1. customby keeping room temperature
  2. additionAfter the addition
  3. stirringthe reaction mixture is stirred for another 30 minutes
  4. customThe reaction mixture is evaporated in vacuo to dryness
  5. customto yield 5.52 g
  6. customThe residue is chromatographed over 500 g of silica gel with hexane/ethylacetate 4/1

Sources & evidence

ORD record
ord-d8d39956d4294c29b770c337c37d04d2
Source dataset
uspto-grants-1999_05
Patent number
US05905074

Reaction notes

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