Sodium borohydride → HCID 117599332, compound

HRID 1466156Notes

Reaction equation

HRID 1466156 reaction equation
[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][C:9](/[CH:11]=[CH:12]/[CH:13]=[O:14])=[CH:10][C:5]=2[CH2:4][O:3]1.[BH4-].[Na+]>C1COCC1.CO.Cl>[OH:14][CH2:13]/[CH:12]=[CH:11]/[C:9]1[CH:8]=[CH:7][C:6]2[C:2](=[O:1])[O:3][CH2:4][C:5]=2[CH:10]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 89526051HCID 89526051, compound

Product 1

HCID 117599332HCID 117599332, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-bath cooled flask containing a solution of (2E)-3-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)prop-2-enal (5 g, 26.6 mmol) in THF (20 mL) and methanol (20 mL) was added NaBH4 (1 g, 26.3 mmol), and the mixture was stirred for 1 hour at 0° C. The reaction mixture was then diluted with HCl (2 N, 20 mL) and extracted with EtOAc (300 mL). The organic layer was washed with water (30 mL) and brine (30 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified with silica gel chromatography (pet ether/EtOAc=2:1) to give the title product.

Workup

  1. temperatureTo an ice-bath cooled flask
  2. extractionextracted with EtOAc (300 mL)
  3. washThe organic layer was washed with water (30 mL) and brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified with silica gel chromatography (pet ether/EtOAc=2:1)

Sources & evidence

ORD record
ord-8208264db50c458eb62848388bca48bf
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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