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

HRID 1514726ノート

反応式

HRID 1514726 の反応式
[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

参加物

8

反応物 5

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 66718302HCID 66718302、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-c0a5e617e74b44bea73a1da3440c846e
出典データセット
uspto-grants-2012_07
特許番号
US08222246B2

反応ノート

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