Diglyme → HCID 21518632, compound

HRID 1283661Notes

Reaction equation

HRID 1283661 reaction equation
[BH4-].[Na+].Cl[CH:4]([C:14]1[O:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[CH:18]=1)[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.COCCOCCOC.[OH-].[Na+]>CCCCCC>[N+:11]([C:8]1[CH:7]=[CH:6][C:5]([CH2:4][C:14]2[O:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[CH:18]=2)=[CH:10][CH:9]=1)([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 8150DiglymeHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 21277827HCID 21277827, compound

Product 1

HCID 21518632HCID 21518632, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 13.6 g. (0.36 mol.) of sodium borohydride and 14.4 g. (0.05 mol.) of 2-(α-chloro-4'-nitrobenzyl)benzofuran in 200 ml. of 80% aqueous diglyme is stirred at 50° for four hours. The reaction mixture is then cooled and hexane followed by 4.0 g. (0.1 mol.) of sodium hydroxide are added. The layers are separated and the organic phase is dried (MgSO4) and concentrated to give 2-(4'-nitrobenzyl)benzofuran.

Workup

  1. additionA mixture of 13.6 g
  2. temperatureThe reaction mixture is then cooled
  3. customThe layers are separated
  4. dry with materialthe organic phase is dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-acbfa2d485984dae98522f9a1299f7bc
Source dataset
uspto-grants-1976_08
Patent number
US03975537

Reaction notes

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