Hexane → 4-(4-Nitrophenyl)butanal

HRID 1192881

반응식

HRID 1192881 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 222697304-(4-Nitrophenyl)butanal수율 72%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 21225700Diisobutylaluminumhydride용매

반응 조건

온도
21 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-34733428100e409580d57abcdcdbd080
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680291B2

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