Sodium borohydride → HCID 22591563, compound

HRID 2101461Notes

Reaction equation

HRID 2101461 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]=[O:11])=[C:7]([CH3:12])[C:6]=2[CH:13]=1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][OH:11])=[C:7]([CH3:12])[C:6]=2[CH:13]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 47369825-Chloro-3-methyl-1-benzofuran-2-carbaldehyde

Product 1

HCID 22591563HCID 22591563, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-chloro-3-methyl benzofuran-2-carboxaldehyde (5.55 mmol, 1.08 g) in ethanol (25 mL) was added portion-wise sodium borohydride (16.6 mmol, 630 mg). After one hour, the ethanol was evaporated and the residue was partitioned between CHCl3 and H2O. The CHCl3 layer was collected, filtered, dried, and evaporated to dryness to obtain 5-chloro-3-methyl benzofuran 2-methanol (88%, 965 mg); mp 112° C.-113° C.

Workup

  1. customthe ethanol was evaporated
  2. customthe residue was partitioned between CHCl3 and H2O
  3. customThe CHCl3 layer was collected
  4. filtrationfiltered
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-e4ada1751f8c4128af6418c915df0196
Source dataset
uspto-grants-2009_08
Patent number
US07572910B2

Reaction notes

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