4-Hydroxybenzaldehyde → 4-(4,4,4-Trifluorobutoxy)benzaldehyde

温度

0 °C

To a solution of 4-hydroxybenzaldehyde (20 g, 164 mmol) and 4,4,4-trifluorobutan-1-ol (25 g, 195 mmol) in anhydrous CH2Cl2 (500 mL) at 0° C. under Ar was added a solution of PPh3 (51.5 g, 196 mmol) in CH2Cl2 (200 mL) over 15 min, and then DIAD (36.4 g, 180 mmol) in anhydrous CH2Cl2 (150 mL) was added dropwise. The mixture was stirred at 0° C. for 0.5 h. The reaction was warmed to rt and stirred for another 3 h. The solvent was removed in vacuo and the residue was triturated with CH2Cl2 three times to remove insoluble solids. The combined CH2Cl2 washings were concentrated and the residue was purified by silica gel chromatography (330 g silica gel, eluted with EtOAc in hexanes) to provide Intermediate 2A (27 g, 71%) as a light brown oil. LCMS Anal. Calc'd for C11H11F3O2 232.20, found [M+H] 233.0.

1. temperatureThe reaction was warmed to rt
2. stirringstirred for another 3 h
3. customThe solvent was removed in vacuo
4. customthe residue was triturated with CH2Cl2 three times
5. customto remove insoluble solids
6. concentrationThe combined CH2Cl2 washings were concentrated
7. customthe residue was purified by silica gel chromatography (330 g silica gel, eluted with EtOAc in hexanes)

ORDレコード

ord-4253b1626534403ba673b7dd1a275090

出典データセット

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08791091B2