Hydrochloric Acid → Ethyl 2-(4-benzyloxyphenyl)cyanoacetate

HRID 398026

반응식

HRID 398026 반응식
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][C:14]#[N:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]CC.[Na+].[C:22](=O)([O:26]CC)[O:23][CH2:24][CH3:25].Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:13]([C:14]#[N:15])[C:22]([O:23][CH2:24][CH3:25])=[O:26])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 5228044-BenzyloxyphenylacetonitrileHCID 2723922Sodium ethoxide

생성물 1

HCID 23001570Ethyl 2-(4-benzyloxyphenyl)cyanoacetate수율 99.2%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

The 4-benzyloxybenzyl cyanide from step (450a)(3.2 g, 14.33 mmol), sodium ethoxide (1.07 g, 15.7 mmol), and diethyl carbonate (2.23 g, 18.9 mmol) were combined in toluene (100 mL), heated to reflux for 3 h, cooled to rt, and partioned between ethyl acetate and 1 N HCl. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The crude was purified by chromatography on silica gel eluting hexane:ethyl acetate (80:20, v:v) to give ethyl 2-(4-benzyloxyphenyl)cyanoacetate (4.2 g, 99%) as an oil. MS (M+NH4)+=313.

후처리

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by chromatography on silica gel
  7. washeluting hexane:ethyl acetate (80:20, v:v)

출처 및 근거

ORD 기록
ord-94741de82d734d9693cabe305f6d8d9d
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610731B2

연결된 노트

불러오는 중…