Triethylamine → [3-(4-Chloro-phenyl)-5-([E]-styryl)-isoxazol-4-yl]-methanol

HRID 1695440Notes

Reaction equation

HRID 1695440 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13](O)=[O:14])=[C:11](/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:10][N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+].[OH-].[Na+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][OH:14])=[C:11](/[CH:16]=[CH:17]/[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 66643754HCID 66643754, compound

Product 1

HCID 66643814[3-(4-Chloro-phenyl)-5-([E]-styryl)-isoxazol-4-yl]-methanolYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(4-chloro-phenyl)-5-([E]-styryl)-isoxazole-4-carboxylic acid (6.0 g, 18.4 mmol) and triethylamine (2.58 mL, 18.4 mmol) in THF (150 mL) was added at room temperature a solution of ethyl chloroformate (1.8 mL, 18.4 mmol) in THF (17.4 mL). After 1 h triethylamine hydrochloride salt was filtered off, and washed with a small amount of THF. The solution was then added to a solution of sodium borohydride (1.82 g, 46.1 mmol) in water (18 mL). After stirring overnight at room temperature sodium hydroxide solution (1 N) was added. Extraction with tert-butylmethylether and purification by chromatography (silica, dichloromethane) afforded the title compound (4.52 g, 79%) as a white solid. MS: m/e=369.9 [M+CH3COO]−.

Workup

  1. filtrationAfter 1 h triethylamine hydrochloride salt was filtered off
  2. washwashed with a small amount of THF
  3. additionwas added
  4. extractionExtraction
  5. customwith tert-butylmethylether and purification by chromatography (silica, dichloromethane)

Sources & evidence

ORD record
ord-52d14c1eed5c4efe839fe9a82ad314b3
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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