Methyl 4-[(tert-butyldimethylsilyl)oxy]-1-methylcyclohexane-1-carboxylate → Methyl 4-hydroxy-1-methylcyclohexane-1-carboxylate

HRID 1504036Notes

Reaction equation

HRID 1504036 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([CH3:19])([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH2:10]1)(C(C)(C)C)(C)C>O1CCCC1>[OH:8][CH:9]1[CH2:10][CH2:11][C:12]([CH3:19])([C:15]([O:17][CH3:18])=[O:16])[CH2:13][CH2:14]1

Participants

3

Reactant 1

HCID 86695195Methyl 4-[(tert-butyldimethylsilyl)oxy]-1-methylcyclohexane-1-carboxylate

Product 1

HCID 13236236Methyl 4-hydroxy-1-methylcyclohexane-1-carboxylateYield 96.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-[(tert-butyldimethylsilyl)oxy]-1-methylcyclohexane-1-carboxylate (10.0 g, 34.91 mmol, 1.00 equiv) in 100 mL of tetrahydrofuran was added TBAF-3H2O (16.5 g, 52.30 mmol, 1.50 equiv) at room temperature and stirred for 5 h. Then the reaction was quenched with water, extracted with 3×100 mL of ethyl acetate. The organic layers were combined, washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/2) to give 5.8 g (96%) of methyl 4-hydroxy-1-methylcyclohexane-1-carboxylate as a light yellow oil.

Workup

  1. customThen the reaction was quenched with water
  2. extractionextracted with 3×100 mL of ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-96b74cd8b4a34bddbbcc45c73cba46f5
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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