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

HRID 1936178Notes

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-4f1f70568f8e42b0a56d80ecf93dbd1b
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06387951B1

Reaction notes

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