Propanal → 2-Methyl-4-(2,2,3-trimethylcyclopent-3-enyl)pent-2-enal

HRID 583638

반응식

HRID 583638 반응식
[CH3:1][C:2]1([CH3:12])[C:6]([CH3:7])=[CH:5][CH2:4][CH:3]1[CH:8]([CH3:11])[CH:9]=O.CC1C(C)(C)[CH:17]([CH2:21][CH:22]=[O:23])CC=1.C(=O)CC.C[O-].[Na+].[Na]>C(O)(=O)C.CO>[CH3:17][C:21](=[CH:9][CH:8]([CH:3]1[CH2:4][CH:5]=[C:6]([CH3:7])[C:2]1([CH3:12])[CH3:1])[CH3:11])[CH:22]=[O:23]

참가 물질

8

반응물 5

HCID 527PropanalHCID 984973-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl-HCID 5360545SodiumHCID 103520572-(2,2,3-Trimethylcyclopent-3-enyl)propionaldehydeHCID 10942334Sodium Methoxide

생성물 1

HCID 572797592-Methyl-4-(2,2,3-trimethylcyclopent-3-enyl)pent-2-enal수율 38%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매

반응 조건

온도
10 °C

실험 절차

60.0 g (0.36 mol) of 2-(2,2,3-trimethylcyclopent-3-enyl)propionaldehyde, prepared from campholenic aldehyde as known per se, and 42.0 g (0.72 mol) of propanal was added successively during 15 min and 2 hours, respectively, to the sodium methylate solution prepared from 0.83 g of sodium and 200 ml of anhydrous methanol, at 10° C. The reaction mixture was stirred at 10° C. for 2 hours and at room temperature for the following 42 hours. After addition of 5 ml of acetic acid the solvent was evaporated in vacuo at the temperature maintained below 50° C. The residue was diluted with 500 ml of MTBE, washed with 2×200 ml of brine, dried (MgSO4), concentrated in vacuo and distilled at 76-95° C./0.1 Torr to give 28.1 g (38%) of 2-methyl-4-(2,2,3-trimethylcyclopent-3-enyl)pent-2-enal. An analytical sample was prepared by flash chromatography on silica gel (eluent: hexane/MTBE 12:1).

후처리

  1. additionwas added successively during 15 min and 2 hours
  2. customwas evaporated in vacuo at the temperature
  3. temperaturemaintained below 50° C
  4. additionThe residue was diluted with 500 ml of MTBE
  5. washwashed with 2×200 ml of brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. distillationdistilled at 76-95° C./0.1 Torr

출처 및 근거

ORD 기록
ord-e0ca7fa447224dd894004f9708336f3f
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05929291

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