Acetic Acid → 2-Cyano-4,4,8-trimethyl-non-2-enoic acid benzyl ester

HRID 28451

반응식

HRID 28451 반응식
[CH3:1][C:2]([CH3:11])([CH2:5][CH2:6][CH2:7][CH:8]([CH3:10])[CH3:9])[CH:3]=O.N1CCCCC1.[C:18]([CH2:20][C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])#[N:19].C(O)(=O)C.Cl>C1(C)C=CC=CC=1>[CH2:24]([O:23][C:21](=[O:22])[C:20]([C:18]#[N:19])=[CH:3][C:2]([CH3:11])([CH3:1])[CH2:5][CH2:6][CH2:7][CH:8]([CH3:10])[CH3:9])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 8082PiperidineHCID 560818Benzyl 2-cyanoacetateHCID 219436612,2,6-Trimethyl-heptanal

생성물 1

HCID 688724612-Cyano-4,4,8-trimethyl-non-2-enoic acid benzyl ester수율 61.6%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a mixture of 2,2,6-Trimethyl-heptanal (1.05 g, 6.73 mmol), piperidine (0.19 mL, 2.01 mmol) and benzyl cyanoacetate (1.29 g, 7.4 mmol) in toluene (50 mL) was added glacial acetic acid (0.72 g, 12.1 mmol). The flask was fitted with a Dean-Stark trap, and the mixture was heated at reflux for 18. The mixture was cooled, treated with dilute HCl, and the layers were separated. The organics were washed with a saturated sodium bicarbonate solution followed by brine, and dried (MgSO4), filtered and concentrated. The residual oil was purified by silica gel chromatography (98/2 hexane/EtOAc) to give 1.3 g of 2-Cyano-4,4,8-trimethyl-non-2-enoic acid benzyl ester m/z 314 (M+).

후처리

  1. customThe flask was fitted with a Dean-Stark trap
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 18
  4. temperatureThe mixture was cooled
  5. customthe layers were separated
  6. washThe organics were washed with a saturated sodium bicarbonate solution
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residual oil was purified by silica gel chromatography (98/2 hexane/EtOAc)

출처 및 근거

ORD 기록
ord-9dc558629ce14142bf4d4ee6b3962698
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419981B2

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