Dimethylformamide → (2R)-2-{[2-(benzyloxy)-4-nitrophenoxy]methyl}oxirane

HRID 1259444Notes

Reaction equation

HRID 1259444 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[OH:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].S(C1C=CC(C)=CC=1)(O[CH2:29][C@@H:30]1[O:32][CH2:31]1)(=O)=O.CN(C=O)C>O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[O:18][CH2:29][C@H:30]1[CH2:31][O:32]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 154187Glycidyl tosylate, (R)-HCID 127366812-(Benzyloxy)-4-nitrophenol

Product 1

HCID 25019918(2R)-2-{[2-(benzyloxy)-4-nitrophenoxy]methyl}oxiraneYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A 500 mL round bottomed flask equipped with a nitrogen inlet and a magnetic stir bar is charged with: 2-(benzyloxy)-4-nitrophenol (10.00 g, 40.8 mmol), potassium carbonate (7.05 g, 51.0 mmol), (R)-(−)-glycidyl tosylate (10.00 g, 43.8 mmol) and DMF (65 mL). The mixture is immersed in an oil bath heated to 60° C. and stirred for 18 h. The solution is allowed to cool to rt, then water (200 mL) is slowly added. The resulting suspension is stirred for 2 h, the precipitate is collected by vacuum filtration and the filter cake is washed with water (25 mL). The cake is dried under suction to yield 10.70 g (87%) of the title compound as a light yellow powder. LCMS (Standard Method): 2.74 min, 302 (M+H)+. 1H NMR (300 MHz, CDCl3) δ 7.89 (dd, J=2.6, 9.0 Hz, 1H), 7.81 (d, J=2.6 Hz, 1H), 7.48-7.34 (m, 5H), 6.98 (d, J=8.8 Hz, 1H), 5.19 (s, 2H), 4.43 (dd, J=2.7, 11.5 Hz, 1H), 4.08 (dd, J=5.8, 11.5 Hz, 1H), 3.43-3.39 (m, 1H), 2.95-2.91 (m, 1H), 2.81-2.78 (m, 1H).

Workup

  1. customA 500 mL round bottomed flask equipped with a nitrogen inlet and a magnetic stir bar
  2. customThe mixture is immersed in an oil bath
  3. temperatureto cool to rt
  4. stirringThe resulting suspension is stirred for 2 h
  5. filtrationthe precipitate is collected by vacuum filtration
  6. washthe filter cake is washed with water (25 mL)
  7. customThe cake is dried under suction

Sources & evidence

ORD record
ord-ef4a537ff76b41d7ad71ae98d8558a52
Source dataset
uspto-grants-2013_06
Patent number
US08466296B2

Reaction notes

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