Sodium borohydride → HCID 13059709, compound

HRID 569014Notes

Reaction equation

HRID 569014 reaction equation
[Br:1][CH:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7]([Cl:13])=[CH:8][CH:9]=2)[S:4][CH2:3]1.[BH4-].[Na+]>CO>[Br:1][CH:2]1[CH:11]([OH:12])[C:10]2[C:5](=[CH:6][C:7]([Cl:13])=[CH:8][CH:9]=2)[S:4][CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13059708HCID 13059708, compound

Product 1

HCID 13059709HCID 13059709, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Suspend 3-bromo-7-chlorothiochroman-4-one (59.6 g., 215 mmole) in methanol (500 mL), cool to 0°-5° C., and with stirring add sodium borohydride (8.18 g., 215 mmole) in three portions. After stirring the reaction mixture at room temperature for three hours, pour it into ice water (4 liters) and extract with chloroform (2 liters). Dry the chloroform solution over anhydrous magnesium sulfate, filter and evaporate in vacuo to a residue. Triturate the residue with chloroform/hexane to give 3-bromo-7-chlorothiochroman-4-ol, mp 141°-142° C.

Workup

  1. temperaturecool to 0°-5° C.
  2. stirringAfter stirring the reaction mixture at room temperature for three hours
  3. extractionextract with chloroform (2 liters)
  4. dry with materialDry the chloroform solution over anhydrous magnesium sulfate
  5. filtrationfilter
  6. customevaporate in vacuo to a residue
  7. customTriturate the residue with chloroform/hexane

Sources & evidence

ORD record
ord-73538381f2964acbabad99036a4e0da1
Source dataset
uspto-grants-1988_03
Patent number
US04731364

Reaction notes

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