Ethyl Acetate → [2-(4-Chloro-2-methoxyphenyl)-4-methylthiazol-5-yl]methanol

HRID 1498914노트

반응식

HRID 1498914 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][C:16]([C:20](O)=[O:21])=[C:17]([CH3:19])[N:18]=2)=[C:10]([O:23][CH3:24])[CH:9]=1.C(OCC)(=O)C>O1CCCC1.C(=O)(O)[O-].[Na+]>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][C:16]([CH2:20][OH:21])=[C:17]([CH3:19])[N:18]=2)=[C:10]([O:23][CH3:24])[CH:9]=1

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 686420482-(4-Chloro-2-methoxyphenyl)-4-methylthiazole-5-carboxylic acid

생성물 1

HCID 68641830[2-(4-Chloro-2-methoxyphenyl)-4-methylthiazol-5-yl]methanol수율 43%

시약·촉매·용매 2

HCID 516892Sodium Bicarbonate촉매2회HCID 8028Tetrahydrofuran용매2회

실험 절차

Lithium aluminum hydride (380 mg, 10.0 mmol) was suspended in tetrahydrofuran (10 ml), and a suspension (10 ml) of 2-(4-chloro-2-methoxyphenyl)-4-methylthiazole-5-carboxylic acid (1.42 g, 5.00 mmol) prepared in Example 7-1 in tetrahydrofuran was added thereto at a room temperature. The mixture was stirred for 3 hours at a room temperature. Under an ice cooling, 5 drops of a saturated sodium bicarbonate solution were slowly added to the mixture. Ethyl acetate was added to the mixture, and another 5 drops of a saturated sodium bicarbonate solution were added thereto. The precipitate was removed by filtration, and the removed solid was washed with chloroform. The washings and the filtrate were concentrated together. The concentrate was purified by silica gel column chromatography (chloroform:methanol=20:1) to give the title compound (580 mg, 43%) as a light-brown powder.

후처리

  1. customat a room temperature
  2. customThe precipitate was removed by filtration
  3. washthe removed solid was washed with chloroform
  4. concentrationThe washings and the filtrate were concentrated together
  5. customThe concentrate was purified by silica gel column chromatography (chloroform:methanol=20:1)

출처 및 근거

ORD 기록
ord-51a779d5609a46cd9dc52d2306de1c7e
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09200008B2

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