Triphenylphosphine → (2R)-2-[(5-Methoxy-2-nitrophenoxy)methyl]oxirane

HRID 270128

Reaction equation

HRID 270128 reaction equation
[O:1]1[CH2:3][C@@H:2]1[CH2:4][OH:5].[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[C:12](O)[CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[C:10]([CH:9]=1)[O:5][CH2:4][C@H:2]1[CH2:3][O:1]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2196355-Methoxy-2-nitrophenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 6973630(-)-Glycidol

Product 1

HCID 86601492(2R)-2-[(5-Methoxy-2-nitrophenoxy)methyl]oxiraneYield 72.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of (2S)-oxiran-2-ylmethanol (296.3 mg, 4.0 mmol), 5-methoxy-2-nitrophenol (676.6 mg, 4.0 mmol) and triphenyl phosphine (1.05 g, 4.0 mmol) in THF (10 mL) was added diethyl azodicarboxylate (DEAD, 704.6 mg, 4.0 mmol) in THF (5 mL) dropwise at room temperature. After addition was completed the reaction mixture was stirred at room temperature overnight. The volatiles were removed in vacuo and the residue was purified by silica gel flash chromatography (040% ethyl acetate in petroleum spirit) to give the subtitled compound (650 mg).

Workup

  1. additionAfter addition
  2. customThe volatiles were removed in vacuo
  3. customthe residue was purified by silica gel flash chromatography (040% ethyl acetate in petroleum spirit)

Sources & evidence

ORD record
ord-a161776fb2e24e1792f765b9ca986115
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Linked notes

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