Trifluoroacetic acid → (2E)-3-{4-[(4-Hydroxyphenyl)(tetrahydro-4H-thiopyran-4-ylidene)methyl]phenyl}-2-propenoic acid

HRID 229156

반응식

HRID 229156 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:24]2[CH2:29][CH2:28][S:27][CH2:26][CH2:25]2)[C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19]C(C)(C)C)=[O:18])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[C:24]2[CH2:25][CH2:26][S:27][CH2:28][CH2:29]2)[C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 689782991,1-Dimethylethyl(2E)-3-{4-[(4-hydroxyphenyl)(tetrahydro-4H-thiopyran-4-ylidene)methyl]phenyl}-2-propenoate

생성물 1

HCID 11348745(2E)-3-{4-[(4-Hydroxyphenyl)(tetrahydro-4H-thiopyran-4-ylidene)methyl]phenyl}-2-propenoic acid

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To an ice-cooled solution of 37 (0.16 g, 0.392 mmol) in dry CH2Cl2 (2 mL) was added TFA (2 mL) slowly. After stirring at 0° C. for 3 h, the reaction mixture was concentrated to give a yellow solid. The crude product was purified by flash column chromatography on silica gel using a CH2Cl2:MeOH gradient (100:0 to 0:100) to give compound 38 a yellow foam (0.074 g, 54%). 1H NMR (400 MHz, DMSO-d6): δ 2.42-2.46 (m, 4H), 2.63-2.66 (m, 4H), 6.46 (d, J=16 Hz, 1H), 6.68 (d, J=8.4 Hz, 2H), 6.87 (d, J=8.5 Hz, 2H), 7.09 (d, J=8.2 Hz, 2H), 7.53 (d, J=15.9 Hz, 1H), 7.59 (d, J=8.2 Hz, 2H), 9.39 (s, 1H), 12.38 (s, 1H). LRMS (ESI) m/z 353 (M+H)+. HRMS (ESI) Calcd for C21H21O3S: 353.1211 (M+H)+. Found: 353.1208.

후처리

  1. concentrationthe reaction mixture was concentrated
  2. customto give a yellow solid
  3. customThe crude product was purified by flash column chromatography on silica gel using a CH2Cl2

출처 및 근거

ORD 기록
ord-8d319811fc7749788b3f7787eb5d4515
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560589B2

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