Dimethylformamide → ethyl (8E)-8-[[4-[(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-8-phenyloctanoate

HRID 2299837노트

반응식

HRID 2299837 반응식
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[O:6][C:7]=1[CH3:8].[OH:14][C:15]1[CH:41]=[CH:40][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.CCCCCC.O>[CH3:8][C:7]1[O:6][C:5]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[N:4][C:3]=1[CH2:2][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:40][CH:41]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 50764914-(Chloromethyl)-5-methyl-2-(thiophen-2-yl)-1,3-oxazoleHCID 22344573ethyl (8E)-8-[(4-hydroxyphenyl)methoxyimino]-8-phenyloctanoate

생성물 1

HCID 22344602ethyl (8E)-8-[[4-[(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-8-phenyloctanoate수율 95%

시약·촉매·용매 2

HCID 962Water용매HCID 21226206Ethyl acetate hexane용매

실험 절차

A mixture of 4-(chloromethyl)-5-methyl-2-(2-thienyl)oxazole (368 mg), ethyl E-8-(4-hydroxybenzyloxyimino)-8-phenyloctanoate (600 mg), potassium carbonate (432 mg) and N,N-dimethylformamide (7 ml) was stirred at room temperature for 18 hours. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain ethyl E-8-[4-[5-methyl-2-(2-thienyl)-4-oxazolylmethoxy]benzyloxyimino]-8-phenyloctanoate (762 mg, yield 95%) as a colorless oil from an ethyl acetate-hexane (1:5, v/v)-eluted fraction.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3e4dc5b25ccc4f0caa27954de323c0e8
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06495581B1

반응 노트

불러오는 중…