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

HRID 1275460Notes

Reaction equation

HRID 1275460 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-913f87102a9c4f4d925a39ce8e5cffa6
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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