4-Nitrophenol → HCID 59444544, compound

HRID 1513998Notes

Reaction equation

HRID 1513998 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([C:13]([O:15][CH3:16])=[O:14])[C:9]([O:11][CH3:12])=[O:10].[N+:17]([C:20]1[CH:25]=[CH:24][C:23](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>C1COCC1>[CH3:16][O:15][C:13]([CH:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:1][C:23]1[CH:24]=[CH:25][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=1)[C:9]([O:11][CH3:12])=[O:10])=[O:14]

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 59444532HCID 59444532, compound

Product 1

HCID 59444544HCID 59444544, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 16 (1.92 g, 8.3 mmol), 4-nitrophenol (1.39 g, 10.0 mmol) and triphenylphosphine (2.62 g, 10.0 mmol) were dissolved in dry THF (100 mL) and deaerated with argon. Diisopropyl azodicarboxylate (2.0 mL, 10.0 mmol) was added in ten portions under argon and the mixture was stirred for 3 days at r.t. The mixture was evaporated to dryness and purified on silica gel (CH2Cl2), yielding 2.6 g (89%) of the title compound.

Workup

  1. customThe mixture was evaporated to dryness
  2. custompurified on silica gel (CH2Cl2)

Sources & evidence

ORD record
ord-c22d0e84f68240a69e558c4b17eafe6c
Source dataset
uspto-grants-2012_07
Patent number
US08221719B2

Reaction notes

Loading…