Dimethylformamide → HCID 22503528, compound

HRID 1814437Notes

Reaction equation

HRID 1814437 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[CH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=[O:19].C(N(CC)CC)C.CN(C)[CH:33]=[O:34]>>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[C:14][C:16]1[CH:23]=[CH:22][C:21]([O:34][CH3:33])=[CH:20][C:17]=1[CH:18]=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 811292-BromobenzaldehydeHCID 563182HEX-5-YNYLOXYMETHYL-BENZENE

Product 1

HCID 22503528HCID 22503528, compound

Procedure

6-Benzyloxy-1-hexyne (5.60 g) and 2-bromo-benzaldehyde (2.90 g) were reacted in dimethylformamide (30 ml), in the presence of dichloro-bis-triphenylphosphinepalladium (0.40 g), cuprous iodide (0.20 g) and triethylamine (2.5 ml) in nitrogen atmosphere at 50° C. for 6 hr. The resulting reaction solution was evaporated, and ethyl acetate and water were added to the resulting residue. The resulting organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give 2.60 g of the title compound as a pale yellow oil. (1-2) 3-(4-Benzyloxybutyl)isoquinoline-2-oxide

Workup

  1. customThe resulting reaction solution
  2. customwas evaporated
  3. additionethyl acetate and water were added to the resulting residue
  4. washThe resulting organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-cc4e552b0ffc4234840b7ec2488d436e
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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