Acetic Acid → methyl (8E)-8-(4-methoxyphenyl)-8-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]octanoate

HRID 584504노트

반응식

HRID 584504 반응식
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][O:20][NH2:21])=[CH:17][CH:16]=1.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=O)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([O:41][CH3:42])=[O:40])=[CH:28][CH:27]=1.C(O)(=O)C.C([O-])(=O)C.[Na+]>C(OCC)(=O)C.CCCCCC.O.CO>[CH3:24][O:25][C:26]1[CH:27]=[CH:28][C:29](/[C:32](=[N:21]/[O:20][CH2:19][C:18]2[CH:17]=[CH:16][C:15]([O:14][CH2:13][C:3]3[N:4]=[C:5]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[O:6][C:2]=3[CH3:1])=[CH:23][CH:22]=2)/[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([O:41][CH3:42])=[O:40])=[CH:30][CH:31]=1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 223445934-(5-Methyl-2-phenyl4-oxazolylmethoxy)benzyloxyamineHCID 22344604Methyl 8-(4-methoxyphenyl)-8-oxooctanoate

생성물 1

HCID 22344576methyl (8E)-8-(4-methoxyphenyl)-8-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]octanoate수율 59%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 21226206Ethyl acetate hexane용매

실험 절차

After a mixture of 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyamine (600 mg), methyl 8-(4-methoxyphenyl)-8-oxooctanoate (538 mg), acetic acid (0.331 ml), sodium acetate (317 mg) and methanol (20 ml) was heated to reflux for 16 hours, the mixture was cooled to room temperature. 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 methyl E-8-(4-methoxyphenyl)-8-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]octanoate (650 mg, yield 59%) as a colorless oil from an ethyl acetate-hexane (2:7, v/v)-eluted fraction.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-32ee95c3f4c24151aba24071d500d62e
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06924300B2

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