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Dichloromethane → Tert-butyl 5-cyclopropyl-2-fluoro-4-((4-oxocyclohexyl)oxy)benzoate

HRID 1849767
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HRID 1849767 반응식
O1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][C:12]3[C:24]([CH:25]4[CH2:27][CH2:26]4)=[CH:23][C:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[C:14]([F:28])[CH:13]=3)[CH2:7][CH2:6]2)[O:4]CC1.FC(F)(F)C(O)=O.ClCCl>O1CCCC1.O>[CH:25]1([C:24]2[C:12]([O:11][CH:8]3[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]3)=[CH:13][C:14]([F:28])=[C:15]([CH:23]=2)[C:16]([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17])[CH2:27][CH2:26]1
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참가 물질

6

반응물 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86703650Tert-butyl 4-(1,4-dioxaspiro[4.5]decan-8-yloxy)-5-cyclopropyl-2-fluorobenzoate

생성물 1

HCID 86703651Tert-butyl 5-cyclopropyl-2-fluoro-4-((4-oxocyclohexyl)oxy)benzoate수율 60%

시약·촉매·용매 2

HCID 962Water용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

To a mixture of tert-butyl 4-(1,4-dioxaspiro[4.5]decan-8-yloxy)-5-cyclopropyl-2-fluorobenzoate (0.557 g, 1.44 mmol) in tetrahydrofuran (1.5 mL) and water (1.5 mL) was added trifluoroacetic acid (0.5 mL) and the reaction mixture was stirred for 16 hours at ambient temperature. After addition of dichloromethane (100 mL), the mixture was washed with saturated sodium bicarbonate solution (10 mL), brine (10 mL), and dried over anhydrous sodium sulfate. Filtration and concentration of the filtrate in vacuo gave a residue which was purified by silica gel column chromatography using 0-30% ethyl acetate in hexanes as eluent to afford the title compound as a colorless oil (0.300 g, 60%): 1H NMR (300 MHz, CDCl3) δ 7.42 (d, J=8.4 Hz, 1H), 6.59 (d, J=12.6 Hz, 1H), 4.80-4.71 (m, 1H), 2.77-2.62 (m, 2H), 2.42-2.27 (m, 4H), 2.14-1.93 (m, 3H), 1.56 (s, 9H), 0.94-0.84 (m, 2H), 0.65-0.60 (m, 2H).

후처리

  1. washthe mixture was washed with saturated sodium bicarbonate solution (10 mL), brine (10 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationFiltration and concentration of the filtrate in vacuo
  4. customgave a residue which
  5. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-0173cdbf2fc74081a10b80924b21b459
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08952169B2

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