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

HRID 1275460노트

반응식

HRID 1275460 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 234506678-Chloro-6-ethoxycarbonyl-5-methylthiochroman-4-ol수율 106.8%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-913f87102a9c4f4d925a39ce8e5cffa6
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06159904

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