Triethylamine → (3-Pyridin-2-yl-isoxazol-4-yl)-methanol
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:11]([C:12](O)=[O:13])=[CH:10][O:9][N:8]=1.C(N(CC)CC)C.C(OC(Cl)=O)C.[BH4-].[Na+]>C1COCC1.O.[OH-].[Na+]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:11]([CH2:12][OH:13])=[CH:10][O:9][N:8]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -10 °C
Procedure
To a solution of 3-pyridin-2-yl-isoxazole-4-carboxylic acid (39.0 g, 200 mmol) in THF (480 mL) at −10° C. was added triethylamine (30.7 mL, 220 mmol) and then a solution of ethylchloroformate (20.0 mL, 210 mmol) in THF (120 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 (18.9 g, 500 mmol) in water (200 mL) added over 15 minutes keeping the temperature below −5° C. The mixture was then allowed to warm up to room temperature over 2 h and diluted with aqueous sodium hydroxide (2 N, 100 mL) and extracted with diethylether. The combined organic layers were then washed with water and brine, dried over sodium sulfate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=1:1 to 1:2) afforded the title product (26.8 g, 76%) which was obtained as white solid. MS: m/e=177.2 [M]+.
Workup
- customthe temperature below −5° C
- filtrationAfter 1 h the mixture was filtered
- additionadded over 15 minutes
- customthe temperature below −5° C
- temperatureto warm up to room temperature over 2 h
- extractionextracted with diethylether
- washThe combined organic layers were then washed with water and brine
- dry with materialdried over sodium sulfate
- customevaporated
- customPurification by chromatography (SiO2, heptane:ethyl acetate=1:1 to 1:2)
Sources & evidence
- ORD record
- ord-dee5322351404dddb8ecee4fdd0e5cc1
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178522B2
Reaction notes
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