Triethylamine → (3-Butyl-isoxazol-4-yl)-methanol

Temperature

-10 °C

To a solution of 3-butyl-isoxazole-4-carboxylic acid (27.8 g, 164 mmol in THF (495 mL) at −10° C. was added triethylamine (22.9 mL, 164 mmol) and then a solution of ethylchloroformate (15.7 mL, 164 mmol) in THF (85 mL) added keeping the temperature below −5° C. After 1 h the mixture was filtered and the filtrate cooled to −10° C. and a suspension of sodiumborohydride (31.1 g, 821 mmol) in water (165 mL) added over 15 minutes keeping the temperature below 10° C. The mixture was then allowed to warm up to room temperature overnight and diluted with sodium hydroxide (2 N, 82 mL) and extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over sodium sulfate and evaporated to afford the title compound (18.6 g, 73%) which was obtained as a colorless liquid after kugelrohr distillation. Bp: 150° C. at 0.4 mbar. MS: m/e=150.1 [M]+.

1. customthe temperature below −5° C
2. filtrationAfter 1 h the mixture was filtered
3. additionadded over 15 minutes
4. customthe temperature below 10° C
5. temperatureto warm up to room temperature overnight
6. extractionextracted with ethyl acetate
7. washThe combined organic layers were then washed with water and brine
8. dry with materialdried over sodium sulfate
9. customevaporated

ORD record

ord-84e3e73fdde646b492e0f40eb9361744

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08357703B2