Chloromethyl Methyl Ether → HCID 23130393, compound

HRID 2080127Notes

Reaction equation

HRID 2080127 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=1[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[CH3:24][O:25][CH2:26]Cl>CS(C)=O.C(OCC)(=O)C.CCCCCC>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=1[O:17][CH2:24][O:25][CH3:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 154534514-(Benzyloxy)-3-hydroxybenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 23130393HCID 23130393, compoundYield 85.3%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8058HexaneSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of the resulting 4-benzyloxy-3-hydroxy-benzonitrile (300 mg, 1.33 mmol) and potassium tert-butoxide (300 mg, 2.66 mmol) in dimethylsulfoxide (4 mL) was added chloromethyl methyl ether (0.204 mL, 2.66 mmol) portionwise under nitrogen atmosphere stirring on an ice bath, and the solution was stirred for 2 days. NH silica gel (25 mL) was added to the reaction solution, purification was carried out by NH silica gel column chromatography (hexane:ethyl acetate=7:3) then silica gel column chromatography (hexane:ethyl acetate=7:3), and the title compound (306 mg, 0.829 mmol, 85.3%) was obtained as a pale yellow solid.

Workup

  1. stirringthe solution was stirred for 2 days
  2. additionNH silica gel (25 mL) was added to the reaction solution, purification

Sources & evidence

ORD record
ord-0e308f1a9137459dac360b5a0715b4d6
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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