Dimethylformamide → HCID 23150777, compound

A mixture of trans-3-(4-fluoro-3-methylphenyl)prop-2-enoic acid (6.18 g) and oxalyl chloride (3.72 mL) in dichloromethane (40 mL) containing N,N-dimethylformamide (60 μL) is stirred at room temperature for three hours, concentrated under reduced pressure and redissolved in tetrahydrofurane (50 mL). The solution is maintained at a temperature below −8° C. during the addition of a suspension of sodium borohydride (2.9 g) in N,N-dimethylformamide (15 mL). The mixture is stirred for one hour at a temperature close to −12° C., hydrolysed by the successive addition of water (10 mL) and 1N hydrochloric acid and extracted with ethyl acetate. The organic layers are pooled, washed with water, dired over magnesium sulfate, concentrated under reduced pressure and purified by chromatography over silica gel, with heptane/ethyl acetate 3/1 as eluant, to give 710 mg of trans-3-(4-fluoro-3-methylphenyl)prop-2-en-1-ol as a colorless oil used without further purification.

1. concentrationconcentrated under reduced pressure
2. dissolutionredissolved in tetrahydrofurane (50 mL)
3. temperatureThe solution is maintained at a temperature below −8° C. during the addition of a suspension of sodium borohydride (2.9 g) in N,N-dimethylformamide (15 mL)
4. stirringThe mixture is stirred for one hour at a temperature
5. customclose to −12° C., hydrolysed by the successive addition of water (10 mL) and 1N hydrochloric acid
6. extractionextracted with ethyl acetate
7. washwashed with water
8. concentrationconcentrated under reduced pressure
9. custompurified by chromatography over silica gel, with heptane/ethyl acetate 3/1 as eluant

ORD record

ord-499f1cd98b434f81b9377022b0928785

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08017646B2