Triphenylphosphine → HCID 67330598, compound

HRID 1942448Notes

Reaction equation

HRID 1942448 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15]([O:20][CH2:21][CH3:22])(=[O:19])[C@H:16]([CH3:18])O.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>O1CCCC1.O>[CH2:21]([O:20][C:15](=[O:19])[C@@H:16]([CH3:18])[O:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13])[CH3:22]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 66835Benzoic acid, 4-hydroxy-3-nitro-, methyl esterHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 92831(L)-ethyl lactate

Product 1

HCID 67330598HCID 67330598, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-hydroxy-3-nitrobenzoate (5.0 g) and ethyl L-lactate (2.9 ml) in tetrahydrofuran (120 ml) was added triphenylphosphine (10 g), and the mixture was stirred at room temperature for 10 minutes. To the mixture was added under ice-cooling diisopropyl azodicarboxylate (20 ml), and the mixture was stirred at 60° C. for 4 hours. The reaction solution was cooled to room temperature, and water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to give the title compound (9.5 g).

Workup

  1. additionTo the mixture was added under ice-
  2. stirringthe mixture was stirred at 60° C. for 4 hours
  3. temperatureThe reaction solution was cooled to room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-5e50d3d924e248c0956dc57732889bc5
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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