Acetic Acid → Methyl (Z)-3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2-(carboxymethoxy)propenoate

HRID 1004193Notes

Reaction equation

HRID 1004193 reaction equation
[H-].[Na+].[C:3]([O:12]C)(=[O:11])[CH2:4][O:5][CH2:6][C:7]([O:9][CH3:10])=[O:8].[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[N:23]([CH2:25][CH2:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1)[CH3:24].C(O)(=O)C>C1C=CC=CC=1.O>[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[N:23]([CH2:25][CH2:26][O:27][C:28]1[CH:35]=[CH:34][C:31](/[CH:32]=[C:6](\[O:5][CH2:4][C:3]([OH:12])=[O:11])/[C:7]([O:9][CH3:10])=[O:8])=[CH:30][CH:29]=1)[CH3:24]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 2018771,1'-Dimethyl 2,2'-oxybis(acetate)HCID 100402134-[2-(N-Methyl-N-(2-benzoxazolyl)amino)ethoxy]benzaldehyde

Product 1

HCID 86753267Methyl (Z)-3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2-(carboxymethoxy)propenoate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of sodium hydride (60% dispersion in mineral oil, 0.30 g), dimethyl diglycolate (0.81 g) and 4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]benzaldehyde (2.22 g) in dry benzene (50 mL) was stirred at room temperature overnight. Acetic acid (1 mL) was added, the mixture was poured onto iced water and extracted with ethyl acetate. The combined ethyl acetate layers were washed with water, dried (MgSO4) and evaporated. The resulting oil was chromatographed on silica gel using 2% methanol in dichloromethane, and the product crystallised from ethyl acetate, mp 111-112° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined ethyl acetate layers were washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe resulting oil was chromatographed on silica gel using 2% methanol in dichloromethane
  6. customthe product crystallised from ethyl acetate, mp 111-112° C.

Sources & evidence

ORD record
ord-3c945fb8302c448c99457677287b8085
Source dataset
uspto-grants-2000_04
Patent number
US06048883

Reaction notes

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