Tetrabutylammonium Fluoride → Ethyl 4-hydroxy-1-methylcyclohexanecarboxylate

HRID 1944719Notes

Reaction equation

HRID 1944719 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([CH3:20])([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][CH:9]1[CH2:10][CH2:11][C:12]([CH3:20])([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58230906Ethyl 4-[(tert-butyldimethylsilyl)oxy]-1-methylcyclohexanecarboxylate2×

Product 1

HCID 58230927Ethyl 4-hydroxy-1-methylcyclohexanecarboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-(tert-butyldimethylsilyloxy)-1-methylcyclohexanecarboxylate (Intermediate 66, 1.32 g, 4.39 mmol) was dissolved in THF (25 ml), to which tetrabutylammonium fluoride (TBAF, 1M solution in THF) (7.34 ml, 7.34 mmol) was added. The reaction mixture was stirred at room temperature overnight, then concentrated and the residue was partitioned between EtOAc/water. The aqueous layer was back extracted and combined organics were dried over MgSO4, filtered and concentrated to afford a brown oil. This material was purified via flash column chromatography, eluting with 2-50% EtOAc/Hept. Relevant fractions were pooled and concentrated to afford a clear oil—797 mg (97% yield).

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. customthe residue was partitioned between EtOAc/water
  4. extractionThe aqueous layer was back extracted
  5. dry with materialcombined organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a brown oil
  9. customThis material was purified via flash column chromatography
  10. washeluting with 2-50% EtOAc/Hept
  11. concentrationconcentrated
  12. customto afford a clear oil—797 mg (97% yield)

Sources & evidence

ORD record
ord-afa0cede615b4bf2a2bd0a5d1eba63f5
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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