Trifluoroacetic acid → Tert-butyl 5-cyclopropyl-2-fluoro-4-((4-oxocyclohexyl)methoxy)benzoate

HRID 1849740ノート

反応式

HRID 1849740 の反応式
O1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][O:12][C:13]3[C:25]([CH:26]4[CH2:28][CH2:27]4)=[CH:24][C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:15]([F:29])[CH:14]=3)[CH2:7][CH2:6]2)[O:4]CC1.FC(F)(F)C(O)=O>O1CCCC1.O.C(OCC)(=O)C>[CH:26]1([C:25]2[C:13]([O:12][CH2:11][CH:8]3[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]3)=[CH:14][C:15]([F:29])=[C:16]([CH:24]=2)[C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:28][CH2:27]1

参加物

6

反応物 2

HCID 6422Trifluoroacetic acidHCID 86703618Tert-butyl 4-(1,4-dioxaspiro[4.5]decan-8-ylmethoxy)-5-cyclopropyl-2-fluorobenzoate

生成物 1

HCID 86703619Tert-butyl 5-cyclopropyl-2-fluoro-4-((4-oxocyclohexyl)methoxy)benzoate収率 96%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of tert-butyl 4-(1,4-dioxaspiro[4.5]decan-8-ylmethoxy)-5-cyclopropyl-2-fluorobenzoate (3.16 g, 7.77 mmol) in tetrahydrofuran (10 mL) and water (10 mL) was added trifluoroacetic acid (2.7 mL) and the reaction mixture was stirred for 16 hours at ambient temperature. After diluting the reaction mixture with ethyl acetate (200 mL), the organic phase was washed with 1 N sodium hydroxide solution (2×15 mL), brine (15 mL), and dried over anhydrous sodium sulfate. Filtration and concentration of the filtrate under reduced pressure gave a residue which was purified by silica gel column chromatography using 0-40% ethyl acetate in hexanes as eluent to afford the title compound as a colorless oil (2.70 g, 96%): 1H NMR (300 MHz, CDCl3) δ 7.37 (d, J=8.4 Hz, 1H), 6.50 (d, J=12.5 Hz, 1H), 3.90 (d, J=6.0 Hz, 2H), 2.53-2.15 (m, 8H), 2.03-1.92 (m, 1H), 1.73-1.59 (m, 1H), 1.55 (s, 9H), 0.92-0.83 (m, 2H), 0.65-0.58 (m, 2H).

後処理

  1. washthe organic phase was washed with 1 N sodium hydroxide solution (2×15 mL), brine (15 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationFiltration and concentration of the filtrate under reduced pressure
  4. customgave a residue which
  5. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-44d39c488120480db7dd616f5c74d0d6
出典データセット
uspto-grants-2015_02
特許番号
US08952169B2

反応ノート

読み込み中…