Benzyl Bromide → HCID 70275183, compound

HRID 1647746Notes

Reaction equation

HRID 1647746 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:16]2[CH2:20][CH2:19][C@H:18]([C:21]3[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=3)[O:17]2)[CH:6]=[C:7]([N+:13]([O-])=O)[C:8]=1[O:9][CH2:10][CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].[CH2:39](Br)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:16]2[CH2:20][CH2:19][C@H:18]([C:21]3[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=3)[O:17]2)[CH:6]=[C:7]([NH:13][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:8]=1[O:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 70277421HCID 70277421, compound

Product 1

HCID 70275183HCID 70275183, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

trans-2-(3-Methoxy-4-propoxy-5-nitrophenyl)-5-(3,4,5-trimethoxyphenyl)-tetrahydrofuran (50 mg, 0.12 mmole) and potassium carbonate (1.0 g) were suspended in 2 mL of DMF. Benzyl bromide (205.1 mg, 1.2 mmole) was added and the suspension was stirred at room temperature for 20 hours. The reaction was quenched with water and extracted with dichloromethane. The organic layer was dried over MgSO4, filtered and evaporated in vacuo to an oil that was purified by column chromatography with hexane/ethyl acetate solvent (yield 50.2 mg, 82.6%).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo to an oil that
  6. customwas purified by column chromatography with hexane/ethyl acetate solvent (yield 50.2 mg, 82.6%)

Sources & evidence

ORD record
ord-e2e037f9c6ed40779012defa90445f8a
Source dataset
uspto-grants-1995_07
Patent number
US05434151

Reaction notes

Loading…