Methanol → HCID 57221674, compound

HRID 1859001Notes

Reaction equation

HRID 1859001 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.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

4

Reactant 2

HCID 887MethanolHCID 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 trimethylsilyljodide by keeping room temperature. After completed addition 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 silicagel 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. additionaddition the reaction mixture
  3. stirringis 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 silicagel with hexane/ethylacetate 4/1

Sources & evidence

ORD record
ord-248accb5894f48688f694933db3d0fc3
Source dataset
uspto-grants-2000_11
Patent number
US06153605

Reaction notes

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