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

HRID 398026

反応式

HRID 398026 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 23001570Ethyl 2-(4-benzyloxyphenyl)cyanoacetate収率 99.2%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-94741de82d734d9693cabe305f6d8d9d
出典データセット
uspto-grants-2003_08
特許番号
US06610731B2

関連ノート

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