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

HRID 1955248

Reaktionsgleichung

Reaktionsgleichung von HRID 1955248
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 23294552Methyl 5-(2-benzyloxy-ethoxy)-2-nitro-benzoateAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ac4f6ec9b9d94a3390bbbd2e71cdb15d
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06124323

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