Chloromethyl Methyl Ether → (+/-) Ethyl 4-[(5,5-dimethyl-8-(methoxymethyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl)azo]benzoate

HRID 965507Notes

Reaction equation

HRID 965507 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][CH:9]([OH:12])[C:8]2[CH:7]=[C:6]([N:13]=[N:14][C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=3)[CH:5]=[CH:4][C:3]1=2.C(NCC)(C)C.[CH3:33][O:34][CH2:35]Cl>C(Cl)Cl>[CH3:26][C:2]1([CH3:1])[CH2:11][CH2:10][CH:9]([O:12][CH2:33][O:34][CH3:35])[C:8]2[CH:7]=[C:6]([N:13]=[N:14][C:15]3[CH:16]=[CH:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][CH:25]=3)[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 88318IsopropylethylamineHCID 22571548Ethyl 4-[(5,5-dimethyl-8-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)azo]benzoate2×

Product 1

HCID 22571546(+/-) Ethyl 4-[(5,5-dimethyl-8-(methoxymethyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl)azo]benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (±) ethyl 4-[(5,5-dimethyl-8-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)azo]benzoate (Compound D5, 49.7 mg, 0.141 mmol) in 4 ml of dry CH2Cl2 at 0° C. was added isopropyl ethyl amine (0.152 ml, 0.847 mmol) followed by chloromethyl methyl ether (0.0323 ml, 0.423 mmol). The reaction mixture was stirred at room temperature for 12 h. Solvent was removed under reduced pressure, the residue was dissolved in ethyl acetate and the solution was washed with NaHCO3 (sat.), and brine. The organic layer was dried (MgSO4). The solvent was removed under reduced pressure, the residue was purified by flash chromatography (silica, ethyl acetate:hexane, 1:3) to afford the title compound as a red oil.

Workup

  1. customSolvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washthe solution was washed with NaHCO3 (sat.), and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by flash chromatography (silica, ethyl acetate:hexane, 1:3)

Sources & evidence

ORD record
ord-870aa10a123b4fbc8a218f019fd1ef54
Source dataset
uspto-grants-1998_06
Patent number
US05773594

Reaction notes

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