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

HRID 1498914ノート

反応式

HRID 1498914 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 516892Sodium Bicarbonate触媒2 回HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-51a779d5609a46cd9dc52d2306de1c7e
出典データセット
uspto-grants-2015_12
特許番号
US09200008B2

反応ノート

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