Ethanol → 4-(2-tert-Butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)-3-fluorobenzaldehyde

HRID 724733

反応式

HRID 724733 の反応式
[C:1]([N:5]1[C:9](=[O:10])[CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([CH:17](Br)Br)=[CH:13][C:12]=2[F:20])[S:6]1(=[O:22])=[O:21])([CH3:4])([CH3:3])[CH3:2].C([OH:25])C>O.[N+]([O-])([O-])=O.[Ag+]>[C:1]([N:5]1[C:9](=[O:10])[CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]=[O:25])=[CH:13][C:12]=2[F:20])[S:6]1(=[O:22])=[O:21])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 702EthanolHCID 116339232-tert-Butyl-5-[4-(dibromomethyl)-2-fluorophenyl]isothiazolidin-3-one 1,1-dioxide

生成物 1

HCID 116166194-(2-tert-Butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)-3-fluorobenzaldehyde収率 83%

試薬・触媒・溶媒 2

HCID 24470Silver Nitrate触媒HCID 962Water溶媒

実験手順

2-tert-Butyl-5-[4-(dibromomethyl)-2-fluorophenyl]isothiazolidin-3-one 1,1-dioxide (4.2 g, 9.2 mmol) and silver nitrate (3.12 g, 18.4 mmol) in ethanol (200 mL) and water (50 mL) were heated at reflux for 0.5 h. The solution was cooled to rt, filtered to remove precipitate, and concentrated to remove most of the ethanol. The residue was diluted with ethyl acetate (200 mL). The organic layer was washed with water (200 mL) and then dried over sodium sulfate. Concentration in vacuo followed by purification by silica gel chromatography (30% ethyl acetate:hexanes) afforded product as a white solid (2.4 g, 83%). 1H NMR (400 MHz, CDCl3): δ 10.0 (d, J=2.0 Hz, 1H), 7.78–7.75 (m,1H), 7.70–7.65 (m, 1H), 7.56–7.52 (m, 1H), 5.13 (dd, J=8.9, 6.6 Hz, 1H), 3.35 (dd, J=17.2, 8.9 Hz, 1H), 3.15 (dd, J=17.2, 6.6 Hz, 1H), 1.66 (s, 9H). LCMS found for C14H17FNNaO4S (M+Na)+: m/z=336.

後処理

  1. temperatureat reflux for 0.5 h
  2. filtrationfiltered
  3. customto remove precipitate
  4. concentrationconcentrated
  5. customto remove most of the ethanol
  6. additionThe residue was diluted with ethyl acetate (200 mL)
  7. washThe organic layer was washed with water (200 mL)
  8. dry with materialdried over sodium sulfate
  9. concentrationConcentration in vacuo
  10. customfollowed by purification by silica gel chromatography (30% ethyl acetate:hexanes)

出典と根拠

ORDレコード
ord-6b74ef2a632e4fca8b875eb97718274f
出典データセット
uspto-grants-2006_11
特許番号
US07141596B2

関連ノート

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