Pyridine → 2-Isopropyl-4-trifluoromethylsulfonyloxy-benzyl acetate

HRID 1070018Notes

Reaction equation

[F:1][C:2]([F:19])([F:18])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[C:9]([CH:15]([CH3:17])[CH3:16])[CH:8]=1)(=[O:5])=[O:4].[C:20](Cl)(=[O:22])[CH3:21].N1C=CC=CC=1>C(Cl)Cl>[C:20]([O:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][S:3]([C:2]([F:18])([F:1])[F:19])(=[O:4])=[O:5])=[CH:8][C:9]=1[CH:15]([CH3:17])[CH3:16])(=[O:22])[CH3:21]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 4-hydroxymethyl-3-isopropylphenyl 1,1,1-trifluoromethanesulfonate (Intermediate 149, 190.0 mg, 0.64 mmol) in 5 mL CH2Cl2 was added acetyl chloride (75.0 mg, 0.96 mmol) and pyridine(101.0 mg, 1.38 mmols). After stirring for 3 hours at 25° C. the reaction was quenched by the addition of H2O and the resulting mixture extracted with EtOAc. The combined organic layers were washed with H2O and saturated aqueous NaCl, dried (MgSO4) and concentrated under reduced pressure. The title compound, 182 mg (84%), was isolated from the residual oil by column chromatography (5-10% EtOAc-hexanes) as a colorless oil.

Workup

customwas quenched by the addition of H2O
extractionthe resulting mixture extracted with EtOAc
washThe combined organic layers were washed with H2O and saturated aqueous NaCl
dry with materialdried (MgSO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-3bb14cb244184d5da5f508e086fffd17
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06252090B1

Reaction notes

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