Dibenzo(b,d)furan-2-carboxaldehyde → 2-Dibenzofuranmethanol

HRID 1620146Notes

Reaction equation

HRID 1620146 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:14]=[O:15].[BH4-].[Na+]>C1COCC1>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:14][OH:15]

Participants

4

Reactant 2

HCID 220843Dibenzo(b,d)furan-2-carboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 2908462-Dibenzofuranmethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dibenzo[b,d]furan-2-carbaldehyde (191 mg, 973 μmol) in THF (10 mL) in a 50 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (37 mg, 0.978 mmol) and the mixture was stirred for 2 h at RT and quenched by adding 10 mL of a 1 N aq. HCl solution. The reaction mixture was stirred at RT for 20 min and extracted with CH2Cl2 (2×50 mL). The organic phase was washed with water (10 mL), brine (10 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum to afford dibenzo[b,d]furan-2-ylmethanol CCH 34116 as an off-white solid (192 mg, 100% yield).

Workup

  1. customquenched
  2. additionby adding 10 mL of a 1 N aq. HCl solution
  3. stirringThe reaction mixture was stirred at RT for 20 min
  4. extractionextracted with CH2Cl2 (2×50 mL)
  5. washThe organic phase was washed with water (10 mL), brine (10 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated at 40° C. under vacuum

Sources & evidence

ORD record
ord-b27249f368fd40b18b28f1140564a95c
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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