Tetrahydrofuran → Methyl 4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)benzoate

HRID 1619181Notes

Reaction equation

HRID 1619181 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:14]([Si](C)(C)C)([F:17])([F:16])[F:15].C1COCC1>CCOCC>[F:15][C:14]([F:17])([F:16])[C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)([OH:3])[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 137990Methyl 4-acetylbenzoateHCID 552549(Trifluoromethyl)trimethylsilane

Product 1

HCID 57892524Methyl 4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)benzoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of methyl 4-acetylbenzoate (5.0 g, 28.1 mmol) and CF3SiMe3 (12.5 mL, 84.2 mmol) in THF (150 mL) TBAF (1.0 M, 78.6 mL, 78.6 mmol) was added dropwise at 0° C. The mixture was then stirred for 2.5 h at room temperature, diluted with Et2O (100 mL). The solution was washed with saturated aqueous NaHCO3 and brine, dried, and concentrated under reduced pressure. Flash chromatography of the residue, using 2:8 EtOAc-hexanes, gave methyl 4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)benzoate: 1H NMR (CDCl3) δ 8.07 (d, J=8.5 Hz, 2H), δ 7.67 (d, J=8.5 Hz, 2H), 3.93 (s, 3H), 2.70 (br, 1H), 1.80 (s, 3H); m/z 249.1 (M+H+).

Workup

  1. additionwas added dropwise at 0° C
  2. washThe solution was washed with saturated aqueous NaHCO3 and brine
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c79a7190bcde4af685f8151e3cf04575
Source dataset
uspto-grants-2014_07
Patent number
US08772296B2

Reaction notes

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