Dimethylformamide → HCID 57431992, compound

HRID 591263Notes

Reaction equation

HRID 591263 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[CH:26]=[O:27]>O1CCCC1>[CH2:12]([O:11][CH2:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH:26]=[O:27])=[CH:3][CH:4]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 219093264-(3-Benzyloxypropyl)bromobenzeneHCID 178418339Butyllithium

Product 1

HCID 57431992HCID 57431992, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl 3-(4-bromophenyl)propyl ether (3.59 g, 11.77 mmol) in tetrahydrofuran (32 mL) at −75° C. under an argon atmosphere was added n-butyllithium (1.6 M in hexane, 8.83 mL). The solution was stirred for 15 min, and N,N-dimethylformamide (1.09 mL, 14.13 mmol) was added dropwise. The reaction was stirred for another 30 min and than warmed to room temperature, quenched with aqueous ammonium chloride solution, extracted with tert-butyl methyl ether and concentrated in vacuo. The crude product was purified on silica gel using a hexane/ethyl acetate gradient, and the appropriate fractions were combined and concentrated.

Workup

  1. stirringThe reaction was stirred for another 30 min
  2. customquenched with aqueous ammonium chloride solution
  3. extractionextracted with tert-butyl methyl ether
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified on silica gel using a hexane/ethyl acetate gradient
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-13a2dbea04494b1590b04db3654edc1c
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

Loading…