Sodium hydride → 4-Cyclopropylmethoxydibenzo[b,d]furan

HRID 1293449Notes

Reaction equation

HRID 1293449 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[C:4]([OH:14])=[CH:3][CH:2]=1.[H-].[Na+].[CH:17]1([CH2:20]Br)[CH2:19][CH2:18]1>CN(C=O)C>[CH:17]1([CH2:20][O:14][C:4]2[C:5]3[O:6][C:7]4[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=4[C:9]=3[CH:1]=[CH:2][CH:3]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 30150514-Dibenzofuranol

Product 1

HCID 692824834-Cyclopropylmethoxydibenzo[b,d]furanYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of Dibenzo[b,d]furan-4-ol (1 g, 5.43 mmol) in DMF (5 ml) was added to a stirred and cooled (0° C.) suspension of 60% sodium hydride (326 mg, 8.12 mmol) in DMF (20 ml). The mixture was stirred at 0° C. for 5 min and cyclopropylmethyl bromide (1.31 g, 10.85 mmol) in DMF (5 ml) was added dropwise over a period of 10 min. The cooling bath was removed and the mixture was stirred for 1 h at room temperature. The reaction mixture was diluted with ice-cold water (100 ml) and extracted with EtOAc (3×50 ml). The combined organic extracts were washed with water (2×100 ml), brine (100 ml) and dried (Na2SO4), to give 1.16 g (90%) of the product as viscous liquid

Workup

  1. temperaturecooled
  2. stirringThe mixture was stirred at 0° C. for 5 min
  3. customThe cooling bath was removed
  4. stirringthe mixture was stirred for 1 h at room temperature
  5. additionThe reaction mixture was diluted with ice-cold water (100 ml)
  6. extractionextracted with EtOAc (3×50 ml)
  7. washThe combined organic extracts were washed with water (2×100 ml), brine (100 ml)
  8. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-cf811004c58441f58ca20fdad893b1af
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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