Water → 8-Chloro-6-ethoxycarbonyl-5-methylthiochroman-4-ol

HRID 1275460ノート

反応式

HRID 1275460 の反応式
[CH3:1][C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:9]([Cl:17])=[C:8]2[C:3]=1[C:4](=[O:18])[CH2:5][CH2:6][S:7]2.[BH4-].[Na+].O>C(O)C>[OH:18][CH:4]1[C:3]2[C:8](=[C:9]([Cl:17])[CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]=2[CH3:1])[S:7][CH2:6][CH2:5]1

参加物

5

反応物 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 109021585-Methyl-6-ethoxycarbonyl-8-chlorothiochroman-4-one

生成物 1

HCID 234506678-Chloro-6-ethoxycarbonyl-5-methylthiochroman-4-ol収率 106.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

13.0 Grams (45.7 mmol) of 5-methyl-6-ethoxycarbonyl-8-chlorothiochroman-4-one was dissolved in 50 ml of ethanol, and 1.73 g (45.7 mmol, 1 eq.) of sodium borohydride was added with an ice bath cooling. The reaction mixture was stirred for 1 hour. After the completion of the reaction, 20 ml of water was added, and the solvent was distilled off. Then, the reaction mixture was extracted with ethyl acetate twice. An organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and the solvent was distilled off to give 14.0 g (yield 100%) of 4-hydroxy-5-methyl-6-ethoxycarbonyl-8-chlorothiochroman.

後処理

  1. temperaturecooling
  2. additionwas added
  3. distillationthe solvent was distilled off
  4. extractionThen, the reaction mixture was extracted with ethyl acetate twice
  5. washAn organic layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off

出典と根拠

ORDレコード
ord-913f87102a9c4f4d925a39ce8e5cffa6
出典データセット
uspto-grants-2000_12
特許番号
US06159904

反応ノート

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