Tributylphosphine → Methyl 5-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinate

HRID 1294150노트

반응식

HRID 1294150 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:16]=[C:17]([CH2:21][OH:22])[CH:18]=[CH:19][CH:20]=1.O[C:24]1[CH:25]=[N:26][CH:27]=[C:28]([CH:33]=1)[C:29]([O:31][CH3:32])=[O:30].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=1)[CH2:21][O:22][C:24]1[CH:25]=[N:26][CH:27]=[C:28]([CH:33]=1)[C:29]([O:31][CH3:32])=[O:30]

참가 물질

6

반응물 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 354317Methyl 5-hydroxypyridine-3-carboxylateHCID 11140977{3-[(5-Methyl-2-Phenyl-1,3-Oxazol-4-Yl)methoxy]phenyl}methanol

생성물 1

HCID 68885855Methyl 5-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinate수율 79%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of [3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]phenyl]methanol (1.92 g), methyl 5-hydroxynicotinate (1.0 g), tributylphosphine (1.98 g) and tetrahydrofuran (100 mL) was added 1,1′-(azodicarbonyl)dipiperidine (2.47 g) at room temperature and the mixture was stirred for 15 hrs. The precipitated crystals were removed by filtration. The filtrate was concentrated and the residue was subjected to silica gel column chromatography to give crystals (2.21 g, 79%) of methyl 5-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinate from a fraction eluted with ethyl acetate-hexane (1:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 96-97° C.

후처리

  1. customThe precipitated crystals were removed by filtration
  2. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-58abafe5bda94b8cb15af00f52df358f
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238716B2

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