Sodium cyanoborohydride → HCID 66632922, compound

HRID 915675Notes

Reaction equation

HRID 915675 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:12]=O)[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[CH:8]=[C:9]([CH2:12][NH2:16])[O:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 1354168999113-85-6

Product 1

HCID 66632922HCID 66632922, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepare a solution of 4-phenyl-2-formylfuran (1.5 g, 8.7 mmol) and MeOH (35 mL). Add NH4OAc (6.7 g, 87.1 mmol) and NaCNBH3 (380 mg, 6.1 mmol). Stir the reaction mixture under nitrogen for 12 hours. Upon completion of the reaction, concentrate the resulting mixture, dilute with water (10 mL), basify with 1 N sodium hydroxide, and extract with diethyl ether (2×10 mL). Dry the organic phase (Na2SO4), filter, and concentrate. Perform flash chromatography on silica gel eluting with 9:1 ethyl acetate/MeOH to afford the title compound (230 mg) as a white solid. 1H NMR (CDCl3) δ 7.65 (s, 1H), 7.46 (d, J=7 Hz, 1H), 7.36 (t, J=7 Hz, 1H), 7.26 (m, 1H), 6.49 (s, 1H), 3.89 (s, 2H), 2.10 (s, 2H).

Workup

  1. customUpon completion of the reaction
  2. concentrationconcentrate the resulting mixture
  3. additiondilute with water (10 mL), basify with 1 N sodium hydroxide
  4. extractionextract with diethyl ether (2×10 mL)
  5. dry with materialDry the organic phase (Na2SO4)
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-b06ea2a4ed944febabde7472e84a33b9
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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