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

HRID 1849767
ノート
印刷プレビュー

反応式

HRID 1849767 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 8028
Tetrahydrofuran
溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0173cdbf2fc74081a10b80924b21b459
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08952169B2

反応ノート

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