Water → HCID 20510018, compound

HRID 1758270Notes

Reaction equation

HRID 1758270 reaction equation
[BH4-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4]1.[OH2:12]>C(O)C>[OH:12][CH:5]([C:10]1[CH:9]=[CH:8][C:7]2[O:3][CH2:4][CH2:5][C:6]=2[CH:11]=1)[CH:6]([CH3:11])[CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 10329DihydrobenzofuranHCID 4311764Sodium borohydride

Product 1

HCID 20510018HCID 20510018, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (1.11 g, 0.029 mol) was added portionwise to a stirred solution of 2,3-dihydrobenzofuran (5.46 g, 0.029 mol) in ethanol (20 cm3) over 0.5 hr. with cooling. The mixture was then stirred at 50°-70° C. for 1.5 hr., cooled, water was added and the mixture was extracted with dichloromethane. The extract was washed with water, dried (Na2SO4), filtered and the solvent was removed. The residue was subjected to column chromatography on silica using toluene as the eluant. The appropriate fractions were combined and the solvent was removed to give 2,3-dihydro-5-(1-hydroxy-2-methyl-1-propyl)benzofuran (5.26 g, 0.027 mol; 95.2%). (Found: C, 74.59; H, 8.33. C12H16O2 requires C, 74.96; H, 8.39%) RF 0.30.

Workup

  1. temperaturewith cooling
  2. temperature, cooled
  3. extractionthe mixture was extracted with dichloromethane
  4. washThe extract was washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was removed
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-caca9bfcf96b4ee6b27e526fcb7464f7
Source dataset
uspto-grants-1983_02
Patent number
US04372970

Reaction notes

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