Potassium borohydride → HCID 57436875, compound

HRID 1724006Notes

Reaction equation

HRID 1724006 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:14])[C:7]([CH3:13])([CH3:12])[CH2:8][O:9]2)=[CH:4][CH:3]=1.[BH4-].[K+]>CO>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([OH:14])[C:7]([CH3:12])([CH3:13])[CH2:8][O:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4192641Potassium borohydrideHCID 57436874HCID 57436874, compound

Product 1

HCID 57436875HCID 57436875, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cooled (0° C.) solution of 7-bromo-3,3-dimethyl-chroman-4-one (1.5 g, 5.91 mmol) in methanol (17 mL) was added potassium borohydride (0.351 g, 6.5 mmol). After completion of addition the reaction stirred at room temperature for 2 hours and was then quenched with 2M HCl (aq.). The aqueous layer was extracted with ethyl acetate (3×) The combined organic layers were dried over sodium sulfate, filtered, and concentrated to yield an off-white solid, which was used in the next step without further purification.

Workup

  1. additionAfter completion of addition the reaction
  2. customwas then quenched with 2M HCl (aq.)
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×) The combined organic layers
  4. dry with materialwere dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield an off-white solid, which
  8. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-4a1574117839432994aeeb3282e4e652
Source dataset
uspto-grants-2009_02
Patent number
US07485283B2

Reaction notes

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