Triphenylphosphine → Methyl 5-(2-benzyloxy-ethoxy)-2-nitro-benzoate

HRID 1955248Notes

Reaction equation

HRID 1955248 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:34]([O:41][CH2:42][CH2:43]O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH2:34]([O:41][CH2:42][CH2:43][O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 121412-(Benzyloxy) ethanolHCID 5462977Diethyl azodicarboxylate2×HCID 12922678Methyl 5-hydroxy-2-nitrobenzoate

Product 1

HCID 23294552Methyl 5-(2-benzyloxy-ethoxy)-2-nitro-benzoateYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-hydroxy-2-nitro-benzoate (7.97 g, 40.43 mmol), triphenylphosphine (12.73 g, 48.53 mmol), and 2-benzyloxyethanol (5.86 ml, 41.24 mmol) in tetrahydofuran (100 ml) was added DEAD (8.04 ml, 95%, 48.51 mmol) dropwise. After addition of the DEAD, the reaction was stirred under nitrogen for 18 h. The solvent was evaporated, benzene was added, and the triphenylphosphine oxide was filtered off. The solid was washed with some benzene, and the filtrate evaporated. The yellow oil was dissolved in minimal benzene, and chromatographed on silica gel eluting with 25% ethyl acetate/hexanes to give methyl 5-(2-benzyloxy-ethoxy)-2-nitro-benzoate (12.47 g, 93%) as a light yellow oil. Analysis calculated for C17H17NO6 : C, 61.63; H, 5.17; N, 4.23. Found: C, 61.46; H, 5.02; N, 4.28.

Workup

  1. customThe solvent was evaporated
  2. additionbenzene was added
  3. filtrationthe triphenylphosphine oxide was filtered off
  4. washThe solid was washed with some benzene
  5. customthe filtrate evaporated
  6. dissolutionThe yellow oil was dissolved in minimal benzene
  7. customchromatographed on silica gel eluting with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-ac4f6ec9b9d94a3390bbbd2e71cdb15d
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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