Chloromethyl Methyl Ether → HCID 14502099, compound

HRID 1722650Notes

Reaction equation

HRID 1722650 reaction equation
[CH2:1]([C:4]1[C:13]([NH:14][C:15](=[O:17])[CH3:16])=[CH:12][CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]=1[OH:18])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH3:26][O:27][CH2:28]Cl>C(Cl)Cl.C(OCC)(=O)C>[CH3:26][O:27][CH2:28][O:18][C:5]1[C:4]([CH2:1][CH:2]=[CH2:3])=[C:13]([NH:14][C:15](=[O:17])[CH3:16])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 8471TriethylamineHCID 10800613Benzoic acid, 4-(acetylamino)-2-hydroxy-3-(2-propenyl)-, methyl ester

Product 1

HCID 14502099HCID 14502099, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 10 g (40.2 mmol) of methyl 3-allyl-4-acetylaminosalicylate in 50 ml of CH2Cl2 is added 7.9 ml (56.3 mmol) of triethylamine in one portion at room temperature, followed by 3.3 ml (44.2 mmol) of chloromethyl methyl ether dropwise at room temperature. Stirring is continued for 24 hours at room temperature. The reaction mixture is diluted with ethyl acetate and washed with water. The organic layer is dried over MgSO4, filtered and concentrated. Flash chromatography (10% EtOAc/hexanes) affords pure methyl 2-methoxymethyloxy-3-allyl-4-acetylaminobenzoate.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-43ce194fa9894b54a45070bcf5ef1917
Source dataset
uspto-grants-1989_08
Patent number
US04857517

Reaction notes

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