3,4-dihydro-2H-pyran → 2-[2-(4-Nitrophenoxy)ethoxy]oxane

HRID 450511Notes

Reaction equation

HRID 450511 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][OH:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][CH2:12][O:13][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][O:14]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 853812-(4-Nitrophenoxy)ethanol

Product 1

HCID 108908362-[2-(4-Nitrophenoxy)ethoxy]oxane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-[(4-Nitrophenyl)oxy]ethanol (1 g, 5.4 mmol), in toluene (50 mL) was added 3,4-dihydro-2H-pyran (1.5 mL) and APTS (catalytic amount). The reaction was stirred at 60° C. for 3 hours. The dark solution was then concentrated and purified by flash chromatography using DCM/cyclohexane 30/70 as eluent. The title compound was obtained as an oil (1.33 g, 92%). LC: Rt: 3.12 min.

Workup

  1. concentrationThe dark solution was then concentrated
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-80ca1934c4ae4791a8d77fa2017e4e93
Source dataset
uspto-grants-2013_07
Patent number
US08486977B2

Reaction notes

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