HCID 21840261, compound → HCID 21840310, compound

HRID 1739049Notes

Reaction equation

HRID 1739049 reaction equation
O[CH:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][C:14]3[N:15]=[C:16]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[O:17][C:18]=3[CH3:19])=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH:3]1[C:26]([O:28][CH3:29])=[O:27]>ClCCl>[CH3:19][C:18]1[O:17][C:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:15][C:14]=1[CH2:13][O:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[CH:2]=[C:3]([C:26]([O:28][CH3:29])=[O:27])[CH2:4][CH2:5]2

Participants

3

Reactant 1

HCID 21840261HCID 21840261, compound

Product 1

HCID 21840310HCID 21840310, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trifluoride diethyl ether complex (4.14 g) was added dropwise to a solution of methyl 1-hydroxy-6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylate (5.46 g) in dichloromethane (200 ml) at 0° C. The mixture was stirred at room temperature for 1 hour. Then, the reaction mixture was washed with water, dried over magnesium sulfate, and concentrated. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform gave methyl 6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3,4-dihydronaphthalene-2-carboxylate (4.30 g, 83%). This product was recrystallized from dichloromethane-isopropyl ether. Colorless prisms, mp: 130-131° C.

Workup

  1. washThen, the reaction mixture was washed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. washThe fractions eluted with chloroform

Sources & evidence

ORD record
ord-d356407ee5174779af5f931929cede0a
Source dataset
uspto-grants-1999_10
Patent number
US05965589

Reaction notes

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