Sodium borohydride → HCID 66643999, compound

HRID 1187085Notes

Reaction equation

HRID 1187085 reaction equation
[CH2:1]([C:4]1[CH:13]=[C:12]([O:14][CH3:15])[C:7]([C:8]([O:10]C)=O)=[C:6]([CH:16]=[O:17])[CH:5]=1)[CH:2]=[CH2:3].[BH4-].[Na+]>CO.CCOC(C)=O>[CH2:1]([C:4]1[CH:13]=[C:12]([O:14][CH3:15])[C:7]2[C:8](=[O:10])[O:17][CH2:16][C:6]=2[CH:5]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 77231251HCID 77231251, compound

Product 1

HCID 66643999HCID 66643999, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a flask charged with methyl 4-allyl-2-formyl-6-methoxybenzoate (0.77 g, 1 mmol) was added sodium borohydride (0.36 g, 9.33 mmol); the mixture was then dissolved in MeOH (10 mL) and stirred for 18 h at room temp. LC indicated completion of the reaction. The mixture was diluted with EtOAc (150 mL) and washed with brine (2×100 mL). The organic layer was then separated, dried(Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified by MPLC (hexanes/EtOAc=1/0.5) to provide 5-allyl-7-methoxy-2-benzofuran-1(3H)-one.

Workup

  1. customcompletion of the reaction
  2. washwashed with brine (2×100 mL)
  3. customThe organic layer was then separated
  4. filtrationdried(Na2SO4), filtered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by MPLC (hexanes/EtOAc=1/0.5)

Sources & evidence

ORD record
ord-2a41b694f2024aa78fc63926bff292c2
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

Loading…