Methyl Benzoate → HCID 45123112, compound

HRID 1446311Notes

Reaction equation

HRID 1446311 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][C:12]1[C:16]([C:17]([OH:19])=[O:18])=[C:15]([CH3:20])[O:14][N:13]=1.[C:21](OC)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC=CC=1.C1COCC1>[CH3:11][C:12]1[C:16]([C:17]([OH:19])=[O:18])=[C:15]([CH2:20][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:14][N:13]=1

Participants

6

Reactant 3

HCID 7150Methyl BenzoateHCID 756363,5-Dimethylisoxazole-4-carboxylic acidHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 45123112HCID 45123112, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium bis(trimethylsilyl)amide (10 g, 60 mmol, 3 eq) in toluene (60 mL) was added drop wise during 15 min to a solution of 3,5-dimethylisoxazole-4-carboxylic acid (2.82 g, 20 mmol) and methyl benzoate (2.5 mL, 1 eq) in THF (20 mL) at a temperature not exceeding 40 deg. After 1 h the reaction was quenched by the addition of a water solution of 0.1M HCl (0.3 L) leaving the water phase still basic and the phases was separated. The water phase was washed with toluene and then reduced in volume by evaporation until most of the residual organic solvents were removed. 1M HCl was added dropwise with stirring. The resulting crystals were filtered and dried in vacuum to yield the title compound. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 2.45 (s, 3H) 4.75 (s, 2H) 7.43-7.51 (m, 2H) 7.55-7.63 (m, 1H) 7.86-8.12 (m, 2H)

Workup

  1. customexceeding 40 deg
  2. customAfter 1 h the reaction was quenched by the addition of a water solution of 0.1M HCl (0.3 L)
  3. customleaving the water phase still basic
  4. customthe phases was separated
  5. washThe water phase was washed with toluene
  6. customreduced in volume by evaporation until most of the residual organic solvents
  7. customwere removed
  8. addition1M HCl was added dropwise
  9. filtrationThe resulting crystals were filtered
  10. customdried in vacuum

Sources & evidence

ORD record
ord-e41452488b6141b1818475d883e414a5
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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