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

HRID 2112734Notes

Reaction equation

HRID 2112734 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.CCOC(/N=N/C(OCC)=O)=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 5462977Diethyl azodicarboxylateHCID 6973630(-)-Glycidol

Product 1

HCID 86601492(2R)-2-[(5-Methoxy-2-nitrophenoxy)methyl]oxiraneYield 60.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of (2S)-oxiran-2-ylmethanol (445 mg, 6.0 mmol), 5-methoxy-2-nitrophenol (1.02 g, 6.0 mmol) and triphenylphosphine (1.57 g, 6.0 mmol) in THF (10 mL) was added DEAD (0.95 mL, 6.0 mmol) in THF (5 mL) dropwise at 0° C. After addition was completed the ice bath was removed and the mixture was stirred at room temperature over night. The volatiles were removed in vacuo and the residue was purified by silica gel flash chromatography (0-40% ethyl acetate in petroleum spirit) to give the sub-title compound (820 mg).

Workup

  1. additionAfter addition
  2. customwas removed
  3. customThe volatiles were removed in vacuo
  4. customthe residue was purified by silica gel flash chromatography (0-40% ethyl acetate in petroleum spirit)

Sources & evidence

ORD record
ord-7e2320e841d34a3eb98056504aacc8eb
Source dataset
uspto-grants-2009_04
Patent number
US07524856B2

Reaction notes

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