Triethylamine → [3-pyridin-2-yl-5([E]-styryl)-isoxazol-4-yl]-methanol

HRID 1514726Notes

Reaction equation

HRID 1514726 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])=[C:10](/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:9][N:8]=1.C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+].[OH-].[Na+]>C1COCC1.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:11]([CH2:12][OH:13])=[C:10](/[CH:15]=[CH:16]/[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[O:9][N:8]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 66718302HCID 66718302, compound

Product 1

HCID 66718169[3-pyridin-2-yl-5([E]-styryl)-isoxazol-4-yl]-methanolYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-pyridin-2-yl-5-([E]-styryl)-isoxazole-4-carboxylic acid (1.1 g, 4 mmol) and triethylamine (0.53 mL, 4 mmol) in THF (15 mL) was added dropwise at room temperature a solution of ethyl chloroformate (0.36 mL, 4 mmol) in THF (15 mL). After 1 h the triethylamine hydrochloride salt was filtered off and washed with a small amount of THF. The filtrate was added to a solution of sodium borohydride (0.36 g, 10 mmol) in water (10 mL). After stirring for 1 h at 5° C. aqueous sodium hydroxide (2 M, 22 mL) was added. Extraction with ethyl acetate, drying over sodium sulfate, filtering and evaporation of the solvent followed by trituration with diisopropylether afforded the title compound (0.76 g, 72%) as a white solid. MS: m/e=279.2 [M+H]+.

Workup

  1. filtrationAfter 1 h the triethylamine hydrochloride salt was filtered off
  2. washwashed with a small amount of THF
  3. additionwas added
  4. extractionExtraction with ethyl acetate
  5. dry with materialdrying over sodium sulfate
  6. filtrationfiltering
  7. customevaporation of the solvent

Sources & evidence

ORD record
ord-c0a5e617e74b44bea73a1da3440c846e
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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