Benzyl Bromide → Benzyl 2-(3-methoxymethoxycarbonylnaphthalen-2-yl)benzoate

HRID 277976

Reaction equation

HRID 277976 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:15][O:16][CH2:17][O:18][C:19]([C:21]1[C:22]([C:31]2[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=2[C:33]([OH:35])=[O:34])=[CH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:20].FC(F)(F)S(OC1C(C(OCOC)=O)=CC2C(=CC=CC=2)C=1)(=O)=O>CN(C)C=O.O>[CH3:15][O:16][CH2:17][O:18][C:19]([C:21]1[C:22]([C:31]2[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=2[C:33]([O:35][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:34])=[CH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:20]

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178093032-(3-(Methoxymethoxycarbonyl)naphthalen-2-yl)benzoic acidHCID 22626196Methoxymethyl 2-trifluoromethylsulfonyloxy-3-naphthalenecarboxylate

Product 1

HCID 22626517Benzyl 2-(3-methoxymethoxycarbonylnaphthalen-2-yl)benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (160 μl) and potassium carbonate (202 mg) were added to a solution of 2-(3-(methoxymethoxycarbonyl)naphthalen-2-yl)benzoic acid (410 mg) which was prepared by the same procedure as a series of reaction of Reference Example 4→Reference Example 5 using methoxymethyl 2-trifluoromethylsulfonyloxy-3-naphthalenecarboxylate, in dimethylformamid (5 ml). The mixture was stirred for 22 hours at room temperature. Water was added to the reaction mixture, and the solution was extracted with ethyl acetate. The extract was washed with water and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=8:2) to give the title compound (498 mg) having the following physical data.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, successively, dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=8:2)

Sources & evidence

ORD record
ord-fb38f4e051b74180a1a2d7e593c54025
Source dataset
uspto-grants-2002_03
Patent number
US06358960B1

Linked notes

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