Sodium cyanoborohydride → HCID 69130046, compound

HRID 915673Notes

Reaction equation

HRID 915673 reaction equation
[C:1]1([C:7]2[C:8]([CH:12]=O)=[CH:9][O:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH3-]C#[N:16].[Na+]>CO>[C:1]1([C:7]2[C:8]([CH2:12][NH2:16])=[CH:9][O:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 150371484-Phenyl-3-furaldehyde

Product 1

HCID 69130046HCID 69130046, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepare a solution of 4-phenyl-3-formylfuran (1.36 g, 7.91 mmol) in methanol (35 mL). Add NH4OAc (6.1 g, 79.1 mmol) and NaCNBH3 (348 mg, 5.54 mmol). Stir the reaction mixture at room temperature under nitrogen for 2.5 days then concentrate the mixture, dilute with water (50 mL), basify with 1 N sodium hydroxide, and extract with methylene chloride (2×100 mL). Dry the organic phase (Na2SO4), filter, and concentrate. Perform flash chromatography on silica gel eluting with 9:1 ethyl acetate/MeOH followed by 100% MeOH to afford 200 mg of the title compound. 1H NMR (CDCl3) δ 7.52 (s, 1H), 7.30-7.46 (m, 6H), 3.87 (s, 2H).

Workup

  1. concentrationthen concentrate the mixture
  2. additiondilute with water (50 mL), basify with 1 N sodium hydroxide
  3. extractionextract with methylene chloride (2×100 mL)
  4. dry with materialDry the organic phase (Na2SO4)
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-09d61f033d6a4e7eb858de3695bc5de4
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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