Diethyl Ether → Ethyl 5-(4-(1-hydroxyethyl)phenyl)-2-benzofurancarboxylate

HRID 1395683Notes

Reaction equation

HRID 1395683 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]3[O:19][C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:17][C:16]=3[CH:25]=2)=[CH:8][CH:7]=1)(=[O:5])[CH3:4].CCOCC>C(O)C>[OH:5][CH:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]3[O:19][C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:17][C:16]=3[CH:25]=2)=[CH:8][CH:7]=1)[CH3:4]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 4311764Sodium borohydrideHCID 20329647Ethyl 5-(4-acetylphenyl)benzofuran-2-carboxylate

Product 1

HCID 20337913Ethyl 5-(4-(1-hydroxyethyl)phenyl)-2-benzofurancarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.2 g of sodium borohydride was added in one portion to a stirred mixture of 15.0 g of 6A, 200 ml of ether and 40 ml of ethanol. The mixture was stirred at room temperature for 2 hours. The solvents were evaporated under reduced pressure. 1.6 liters of water was added to the residue and the mixture was extracted with chloroform. The extract was dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The residue was dissolved in 150 ml of chloroform. The solution was filtered through charcoal. 400 ml of hexane was added. The solid which formed was collected, recrystallized from a 3/50 v/v mixture of chloroform and hexane and dried in a vacuum oven to give ethyl 5-(4-(1-hydroxyethyl)phenyl)-2-benzofurancarboxylate (6B), mp: 108°-109° C.

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. addition1.6 liters of water was added to the residue
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialThe extract was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. dissolutionThe residue was dissolved in 150 ml of chloroform
  8. filtrationThe solution was filtered through charcoal
  9. addition400 ml of hexane was added
  10. customThe solid which formed
  11. customwas collected
  12. customrecrystallized from a 3/50 v/v mixture of chloroform and hexane
  13. customdried in a vacuum oven

Sources & evidence

ORD record
ord-f2806e7ba71e403b839e4f450a74392b
Source dataset
uspto-grants-1980_05
Patent number
US04205080

Reaction notes

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