Chloromethyl Methyl Ether → HCID 10977800, compound

HRID 1048738Notes

Reaction equation

HRID 1048738 reaction equation
[CH3:1][O:2][CH2:3]Cl.[OH:5][C:6]1[CH:7]=[C:8]([CH:18]=[O:19])[CH:9]=[C:10]2[C:15]=1[O:14][C:13]([CH3:17])([CH3:16])[CH:12]=[CH:11]2.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH3:1][O:2][CH2:3][O:5][C:6]1[CH:7]=[C:8]([CH:18]=[O:19])[CH:9]=[C:10]2[C:15]=1[O:14][C:13]([CH3:16])([CH3:17])[CH:12]=[CH:11]2

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 11052728HCID 11052728, compound

Product 1

HCID 10977800HCID 10977800, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloromethyl methyl ether (4 mL, 5 mmol) was added to a solution of 9 (103 mg, 0.5 mmol) and N,N-diisopropylethylamine (0.2 mL, 1 mmol) in 4 mL of methylene chloride. The reaction mixture was refluxed overnight and concentrated in vacuo. 10 (48 mg, 38%) was purified with ethyl acetate/hexane (1/50). 1H NMR (CDCl3): δ 1.52 (s, 6H), 3.54 (s, 3H), 5.25 (s, 2H), 5.71 (d, J=9.67 Hz, 1H), 6.38 (d, J=9.96 Hz, 1H), 7.26 (d, J=1.76 Hz, 1H), 7.52 (d, J=1.76 Hz, 1H), 9.80 (s, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. concentrationconcentrated in vacuo
  3. custom10 (48 mg, 38%) was purified with ethyl acetate/hexane (1/50)

Sources & evidence

ORD record
ord-4ff87e4675a846d3bde1ee18bf093303
Source dataset
uspto-grants-2016_07
Patent number
US09381260B2

Reaction notes

Loading…