HCID 921579, compound → (1-Benzofuran-2-yl)(4-nitrophenyl)methanol

HRID 1283660Notes

Reaction equation

HRID 1283660 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:22]=[CH:21][C:9]([C:10]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[CH:16]=2)=[O:11])=[CH:8][CH:7]=1)([O-:5])=[O:4]>CO>[OH:11][CH:10]([C:12]1[O:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[CH:16]=1)[C:9]1[CH:21]=[CH:22][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 921579HCID 921579, compoundHCID 4311764Sodium borohydride

Product 1

HCID 199007(1-Benzofuran-2-yl)(4-nitrophenyl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (7.4 g., 0.2 mol.) is added portionwise to a rapidly stirred solution of 26.7 g. (0.1 mol.) of 2-(4'-nitrobenzoyl)benzofuran in methanol. The reaction mixture stirred at 25° for one hour then quenched by addition of water. The aqueous slurry is extracted with chloroform, the extracts are dried (MgSO4) and the solvent is removed in vacuo to give 2-(α-hydroxy-4'-nitrobenzyl)benzofuran which is immediately converted to the corresponding α-chloride by reaction with 14.3 g. (0.12 mol.) of thionyl chloride.

Workup

  1. customthen quenched by addition of water
  2. extractionThe aqueous slurry is extracted with chloroform
  3. dry with materialthe extracts are dried (MgSO4)
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-691be4e32ab149428c14acaaa3c37a33
Source dataset
uspto-grants-1976_08
Patent number
US03975537

Reaction notes

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