Acetic Acid → 6-(3-Hydroxymethyl-phenyl)-hexanoic Acid Methyl Ester

HRID 988252Notes

Reaction equation

HRID 988252 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](C2C=CC=CC=2)(C2C=CC=CC=2)[O:16][SiH2]C(C)(C)C)[CH:10]=1.C(O)(=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O.CCOCC>[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][OH:16])[CH:10]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 131724102Methyl 6-[3-[tert-butylsilyloxy(diphenyl)methyl]phenyl]hexanoate

Product 1

HCID 541865116-(3-Hydroxymethyl-phenyl)-hexanoic Acid Methyl EsterYield 94.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584169Diethylether ethylacetateSolvent

Procedure

To a solution of 6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-phenyl]-hexanoic acid methyl ester (2.37 g, 5 mmol) in THF (10 mL) is added acetic acid (283 μL, 5 mmol) and 1M TBAF (5 mL). The solution is stirred for 2 hrs then diluted with EtOAc/ether (1:1). The organic layer is washed with water, brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 35% ethyl acetate/hexanes) to give 1.12 g of title compound. MS (EI) 236 (M+).

Workup

  1. washThe organic layer is washed with water, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue is purified by flash chromatography (eluting with 35% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-7c93be5cf3be40b1a604109e505e9399
Source dataset
uspto-grants-2003_10
Patent number
US06635655B1

Reaction notes

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