Phenol → 2-(5-Nitro-2-phenoxy-benzyloxy)-tetrahydro-pyran

HRID 1796629Notes

Reaction equation

HRID 1796629 reaction equation
F[C:2]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:3]=1[CH2:4][O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7]1.[C:19]1([OH:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CC([O-])(C)C.[K+]>C1(C)C=CC=CC=1.O>[N+:16]([C:13]1[CH:14]=[CH:15][C:2]([O:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:3]([CH:12]=1)[CH2:4][O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7]1)([O-:18])=[O:17]

Participants

6

Reactant 3

HCID 996PhenolHCID 221796312-(2-Fluoro-5-nitro-benzyloxy)-tetrahydro-pyranHCID 23665647Potassium tert-butoxide

Product 1

HCID 221794762-(5-Nitro-2-phenoxy-benzyloxy)-tetrahydro-pyranYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 394B (125 mg, 0.49 mmol), phenol (55 mg, 0.59 mmol) and t-BuOK (65 mg, 0.58 mmol) in toluene (1 ml) was heated at 120° C. for 2 h. and then diluted with water, extracted with EtOAc, dried and concentrated to give 394C (145 mg, 90%).

Workup

  1. extractionextracted with EtOAc
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-75d934913ebe4b29a775d5371b5102d4
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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