Ammonium Chloride → 4-Hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

HRID 1792369Notes

Reaction equation

HRID 1792369 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:22])[C:8]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)([CH3:13])[CH2:9][S:10]2)=[CH:5][CH:4]=1.[BH4-].[Na+].[NH4+].[Cl-]>C1COCC1.CCO>[OH:22][CH:7]1[C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[S:10][CH2:9][C:8]1([C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[CH3:13]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 10979954HCID 10979954, compound

Product 1

HCID 220333534-Hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochromanYield 84.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-one (6.29 g, 20 mmol) in THF (20 ml) and EtOH (10 ml) was added NaBH4 (1.51 g, 40 mmol), which was stirred overnight at room temperature. The reaction solution was added saturated aqueous NH4Cl solution, extracted with CHCl3, and washed with brine. The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. The residue was purified by recrystallization with CHCl3-hexane to give 5.33 g (84%) of 4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman.

Workup

  1. extractionextracted with CHCl3
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by recrystallization with CHCl3-hexane

Sources & evidence

ORD record
ord-7b71317802264f7b9f5ec3409093907e
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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