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

HRID 400127

반응식

HRID 400127 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 241Benzene용매HCID 962Water용매

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-1fbb035dd18a420b811f3166580f7d15
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05827865

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