Potassium Carbonate → (R)-5-trifluoromethyl-2-(2,3-epoxypropoxy)benzaldehyde

HRID 369077Notes

Reaction equation

C1(C)C=CC(S(O[CH2:11][C@@H:12]2[O:14][CH2:13]2)(=O)=O)=CC=1.[F:16][C:17]([F:28])([F:27])[C:18]1[CH:19]=[CH:20][C:21]([OH:26])=[C:22]([CH:25]=1)[CH:23]=[O:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cl-].[Na+].O>[F:16][C:17]([F:27])([F:28])[C:18]1[CH:19]=[CH:20][C:21]([O:26][CH2:11][C@@H:12]2[O:14][CH2:13]2)=[C:22]([CH:25]=1)[CH:23]=[O:24]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of (R)-glycidyl 4-toluenesulphonate (24 g), 5-trifluoromethyl-2-hydroxybenzaldehyde (20 g) and potassium carbonate (16 g) in dimethylformamide (550 ml) was stirred and heated at 60° C. for 72 hours. After cooling, brine (1.5 L) was added and the resultant mixture extracted with ether (4×500 ml). The combined ether extracts were washed with brine (2×500 ml), then water (500 ml) and dried over magnesium sulphate. The residue was purified by flash column chromatography on silica eluting with a 3:1 mixture of petroleum ether (b.p. 40-60 ° C.) and ethyl acetate to give (R)-5-trifluoromethyl-2-(2,3-epoxypropoxy)benzaldehyde (18.7 g) as a yellow oil.

Workup

temperatureAfter cooling
extractionthe resultant mixture extracted with ether (4×500 ml)
washThe combined ether extracts were washed with brine (2×500 ml)
dry with materialwater (500 ml) and dried over magnesium sulphate
customThe residue was purified by flash column chromatography on silica eluting with a 3:1 mixture of petroleum ether (b.p. 40-60 ° C.) and ethyl acetate

Sources & evidence

ORD record: ord-c62a18a3333d4ff6aa2cee95149e7f62
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06136825

Reaction notes

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