Hexane → 4-(4-Nitrophenyl)butanal

HRID 1192881

反応式

HRID 1192881 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13](OC)=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].CCCCCC>ClCCl.[H-].C([Al+]CC(C)C)C(C)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][CH:13]=[O:14])=[CH:8][CH:9]=1)([O-:3])=[O:2]

参加物

5

反応物 2

HCID 8058HexaneHCID 140721Methyl 4-(4-nitrophenyl)butanoate

生成物 1

HCID 222697304-(4-Nitrophenyl)butanal収率 72%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 21225700Diisobutylaluminumhydride溶媒

反応条件

温度
21 °C

実験手順

To a stirred solution of methyl 4-(4-nitrophenyl)butanoate (63) (0.45 g, 2.02 mmol) in dichloromethane (30 mL), 1M diisobutylaluminum hydride (DIBAL) solution in hexane (2.62 mL, 2.62 mmol) was added at −78° C. After 30 min, the reaction mixture was quenched with saturated Rochelle's salt solution. The resulting mixture was stirred at 21° C. until both phases were clearly separated and the organic layer was clear. After extraction, the separated organic layer was dried over MgSO4, filtered, and concentrated under vacuum. The crude 4-(4-Nitrophenyl)butanal (64) was purified by flash column chromatography (hexane:ethyl acetate, 8:1) to give 4-(4-Nitrophenyl)butanal (64) (0.28 g, 72%): 1H NMR δ 9.79 (s, 1H), 8.16 (d, 2H, J=8.7 Hz) 7.34 (d, 2H, J=8.7 Hz) 2.77 (t, 2H, J=7.7 Hz) 2.51 (t, 2H, J=7.1 Hz), 1.95-2.04 (m, 2H).

後処理

  1. customthe reaction mixture was quenched with saturated Rochelle's salt solution
  2. customwere clearly separated
  3. extractionAfter extraction
  4. dry with materialthe separated organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude 4-(4-Nitrophenyl)butanal (64) was purified by flash column chromatography (hexane:ethyl acetate, 8:1)

出典と根拠

ORDレコード
ord-34733428100e409580d57abcdcdbd080
出典データセット
uspto-grants-2014_03
特許番号
US08680291B2

関連ノート

読み込み中…