4-Nitrophenethyl alcohol → HCID 68505359, compound

HRID 1256891Notes

Reaction equation

HRID 1256891 reaction equation
[CH:1]([C:12]([O:14][CH2:15][CH3:16])=[O:13])([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]([O:4][CH2:5][CH3:6])=[O:3].[N+:17]([C:20]1[CH:28]=[CH:27][C:23]([CH2:24][CH2:25]O)=[CH:22][CH:21]=1)([O-:19])=[O:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(C)C=CC=CC=1>CCOCC>[N+:17]([C:20]1[CH:28]=[CH:27][C:23]([CH2:24][CH2:25][C:1]([C:12]([O:14][CH2:15][CH3:16])=[O:13])([C:2]([O:4][CH2:5][CH3:6])=[O:3])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:22][CH:21]=1)([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 74944-Nitrophenethyl alcoholHCID 11776TriphenylphosphineHCID 80471Triethyl methanetricarboxylateHCID 66880968DIAD toluene

Product 1

HCID 68505359HCID 68505359, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of triethyl methanetricarboxylate (16.6 g) in ether (350 mL) were added 4-nitrophenethyl alcohol (8.00 g) and triphenylphosphine (25.0 g). 40% Diisopropyl azodicarboxylate/toluene solution (48.4 g) was added dropwise to the mixture under ice-cooling, and the mixture was stirred at room temperature for 18 hr. Insoluble material was removed by filtration, and the filtrate was washed with saturated aqueous sodium hydrogen carbonate solution (300 mL) and saturated brine. After concentration under reduced pressure, the residue was purified by silica gel column chromatography to give the title compound (12.2 g) as an oil.

Workup

  1. temperaturecooling
  2. customInsoluble material was removed by filtration
  3. washthe filtrate was washed with saturated aqueous sodium hydrogen carbonate solution (300 mL) and saturated brine
  4. concentrationAfter concentration under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e5d0db655c974bb6b63e079de14f0a7f
Source dataset
uspto-grants-2013_06
Patent number
US08461209B2

Reaction notes

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