Hydrochloric Acid → 8-Chloro-6-ethoxycarbonyl-5-methylthiochroman-4-ol

HRID 368949ノート

反応式

HRID 368949 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]([CH3:13])=[C:6]2[C:11]=1[S:10][CH2:9][CH2:8][C:7]2=[O:12].[BH4-].[Na+].Cl>C(O)C.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]([CH3:13])=[C:6]2[C:11]=1[S:10][CH2:9][CH2:8][CH:7]2[OH:12]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 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 97.3%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒

実験手順

88.4 g (311 mmol) of the 8-chloro-6-ethoxycarbonyl-5-methylthiochroman-4-one obtained in the above step (5) was dissolved in 200 ml of ethanol, and further dissolved in 200 ml of dichloromethane. This solution was cooled to 5~10° C., and 5.9 g (155 mmol) of sodium borohydride was added. The reaction mixture was stirred at the above temperature for 30 minutes, and further stirred at room temperature for 3 hours. Then, the reaction mixture was poured into 400 ml of a 5% hydrochloric acid aqueous solution and extracted with 900 ml of dichloromethane, and then the resultant organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off to give 86.8 g (yield 97%) of 8-chloro-6-ethoxycarbonyl-5-methylthiochroman-4-ol.

後処理

  1. temperatureThis solution was cooled to 5~10° C.
  2. stirringfurther stirred at room temperature for 3 hours
  3. extractionextracted with 900 ml of dichloromethane
  4. washthe resultant organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off

出典と根拠

ORDレコード
ord-fc59b914660a4364be7547ee03dd3b6a
出典データセット
uspto-grants-2000_10
特許番号
US06136755

反応ノート

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