Benzyl Chloride → 6-Benzyloxy-benzo[d]isoxazole-3-carboxylic acid ethyl ester

HRID 556342

Reaction equation

HRID 556342 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[O:8][N:7]=1)=[O:5])[CH3:2].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O.CCOC(C)=O.O>[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][C:9]=2[O:8][N:7]=1)=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 7503Benzyl ChlorideHCID 10796Cesium carbonateHCID 136216618Ethyl 6-hydroxybenzo[d]isoxazole-3-carboxylate

Product 1

HCID 669926006-Benzyloxy-benzo[d]isoxazole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
56 °C

Procedure

To a solution of 0.98 g (4.73 mMol) 6-hydroxy-benzo[d]isoxazole-3-carboxylic acid ethyl ester [preparation see: J. Am. Chem. Soc. 97 (1974), 7305] in 100 ml acetone, 545 μl (4.73 mMol) benzylchloride, 3.08 g (9.46 mMol) Cs2CO3 und 10 mg NaI are added. Then the mixture is stirred for 2 h at rt and 5 h at 56° C. The reaction mixture is diluted with EtOAc and water, the aq. phase separated off and extracted with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated after addition of 10 g SiO2. The resulting powder is put on top of a chromatography column (SiO2) and the title compound eluated with hexan/EtOAc 9:1→8:2→7:3: MS: [M+1]+=298; TLC(hexane/EtOAc 3:1): Rf=0.54.

Workup

  1. customthe aq. phase separated off
  2. extractionextracted with EtOAc
  3. washThe organic layers are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. additionafter addition of 10 g SiO2

Sources & evidence

ORD record
ord-d50dad6058f1460a8e5533089bfa5bdd
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Linked notes

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