Potassium borohydride → HCID 57436875, compound

HRID 2382569Notes

Reaction equation

HRID 2382569 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-efcf9deabf4544fdb0de77cf2152cfff
Source dataset
uspto-grants-2012_09
Patent number
US08263042B2

Reaction notes

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