Tetrabutylammonium Fluoride → 1-(5-(4-Hydroxyphenyl)oxazol-2-yl)-7-phenylheptan-1-one

HRID 605638노트

반응식

HRID 605638 반응식
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][C:14]([CH:16]([O:29][Si](C(C)(C)C)(C)C)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:13][CH:12]=2)=[CH:7][CH:6]=1)(=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>CCOC(C)=O>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[O:15][C:14]([C:16](=[O:29])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[N:13][CH:12]=2)=[CH:9][CH:10]=1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 670460444-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)phenyl acetate

생성물 1

HCID 161106461-(5-(4-Hydroxyphenyl)oxazol-2-yl)-7-phenylheptan-1-one수율 11.6%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

The title compound was prepared from 4-(2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)phenyl acetate (30 mg, 0.059 mmol) following General Procedure D except the reaction with Bu4NF stirred for 5 h. Preparative thin layer chromatography (40% EtOAc) yielded the title compound as a white solid (2.4 mg, 10%): 1H NMR (CDCl3, 600 MHz) δ 7.66 (d, 2H, J=8.4 Hz), 7.37 (s, 1H), 7.27-7.25 (m, 2H), 7.17-7.16 (m, 3H), 6.91 (d, 2H, J=8.4 Hz), 3.06 (t, 2H, J=7.5 Hz), 2.60 (t, 2H, J=7.5 Hz), 1.79-1.75 (m, 2H), 1.65-1.61 (m, 2H), 1.43-1.38 (m, 4H); 13C NMR (CD3OD, 125 MHz) δ 188.7, 161.1, 159.2, 157.7, 143.1, 128.8, 128.7, 127.6, 126.0, 122.7, 120.0, 116.6, 39.3, 36.3, 31.7, 29.5, 29.4, 24.5; MALDI-FTMS m/z 350.1748 (M+H+, C22H24NO3, requires 350.1751).

출처 및 근거

ORD 기록
ord-949405753d1243178ba64fcd925f7c2d
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915270B2

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