Water → 2-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-thiazole-5-carboxylic acid ethyl ester

HRID 1923639노트

반응식

HRID 1923639 반응식
[H-].[Na+].[CH3:3][C:4]1[O:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]=1[CH2:15][OH:16].[CH2:17]([O:19][C:20]([C:22]1[S:26][C:25](Cl)=[N:24][CH:23]=1)=[O:21])[CH3:18].O>O1CCCC1>[CH2:17]([O:19][C:20]([C:22]1[S:26][C:25]([O:16][CH2:15][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N:7][O:8][C:4]=2[CH3:3])=[N:24][CH:23]=1)=[O:21])[CH3:18]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanolHCID 19017727Ethyl 2-chloro-1,3-thiazole-5-carboxylate

생성물 1

HCID 595684942-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-thiazole-5-carboxylic acid ethyl ester수율 52%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred suspension of sodium hydride (304 mg, 6.98 mmol, 60% dispersion in mineral oil) in tetrahydrofuran (30 mL) at 0° C. under argon was added (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (1.0 g, 5.28 mmol) The mixture was warmed to room temperature and after 1 h the reaction mixture was cooled to 0° C. then a solution of 2-chloro-thiazole-5-carboxylic acid ethyl ester (1.01 g, 5.28 mmol) in THF (15 mL) added. The reaction mixture was warmed to room temperature and after 15 h, water (20 mL) was added and the resulting mixture extracted with ethyl acetate. The combined organic extracts were dried, filtered and concentrated. Purification by chromatography (silica, 20% ethyl acetate in heptane) gave the title compound (940 mg, 52% yield) as an off-white solid. MS: m/e=345.0 [M+H]+.

후처리

  1. temperaturewas cooled to 0° C.
  2. temperatureThe reaction mixture was warmed to room temperature and after 15 h
  3. extractionthe resulting mixture extracted with ethyl acetate
  4. customThe combined organic extracts were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by chromatography (silica, 20% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-e204716e625e4753843b7c04b8808360
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178522B2

반응 노트

불러오는 중…