Triphenylphosphine → HCID 57420494, compound

HRID 1271200Notes

Reaction equation

HRID 1271200 reaction equation
[N+:1]([C:4]1[C:5]([OH:14])=[C:6]([O:12][CH3:13])[CH:7]=[C:8]([CH:11]=1)[CH:9]=[O:10])([O-:3])=[O:2].[C:15]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:16]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:20]([O:19][C:15](=[O:18])[CH2:16][O:14][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[O:12][CH3:13])[CH3:21]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 12184Ethyl GlycolateHCID 811345-NitrovanillinHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 57420494HCID 57420494, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of 5-nitrovanillin (2.00 g, 10.11 mmol) in tetrahydrofuran (100 mL) was added ethyl glycolate (0.960 mL, 10.11 mmol), triphenylphosphine (3.84 g, 14.65 mmol), and dropwise addition of diethyl azodicarboxylate (2.70 mL, 17.10 mmol). The reaction was stirred overnight at room temperature. The solution was then concentrated in under reduced pressure to yield a crude oil. Purification of the residue by silica gel flash chromatography (20% ethyl acetate/hexane to 40% ethyl acetate/hexane) afforded the title compound. 1H NMR (d6-DMSO) δ 1.15 (t, 3H), 3.94 (s, 3H), 4.10 (q, 2H), 4.93 (s, 2H), 7.79 (d, 1H), 8.02 (d, 1H), 9.94 (s, 1H). MS: M++1=284.2 Da.

Workup

  1. concentrationThe solution was then concentrated in under reduced pressure
  2. customto yield a crude oil
  3. customPurification of the residue by silica gel flash chromatography (20% ethyl acetate/hexane to 40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f426294b78da421f8e92da81b35a432b
Source dataset
uspto-grants-2007_04
Patent number
US07205295B2

Reaction notes

Loading…