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Ethyl formate → Benzyl 2-chloro-3-oxopropanoate

HRID 79318
ノート
印刷プレビュー

反応式

HRID 79318 の反応式
C[C:2](C)([O-:4])C.[K+].[Cl:7][CH2:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].C(OCC)=O>CCOCC>[Cl:7][CH:8]([CH:2]=[O:4])[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8025Ethyl formateHCID 8786Acetic acid, 2-chloro-, phenylmethyl esterHCID 23665647Potassium tert-butoxide

生成物 1

HCID 86672210Benzyl 2-chloro-3-oxopropanoate

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To potassium tert-butoxide (141 mL, 141 mmol) at 0° C. was added dropwise a solution of benzyl 2-chloroacetate (26.8 g, 141 mmol) and ethyl formate (11.6 mL, 141 mmol) in Et2O (45 mL). The reaction was warmed to ambient temperature and stirred for 16 hours. The reaction mixture was filtered and washed with cold ether (100 mL). The potassium salt was dissolved in H2O (50 mL) and the solution was acidified with concentrated HCl to pH=4 in a cold bath. The solution was extracted with ether and the organic phase was dried (MgSO4) and concentrated to give the crude product. A lower boiling point impurity was removed by vacuum distillation (90° C., 5 mm Hg) and the residue was taken directly to the next step.

後処理

  1. filtrationThe reaction mixture was filtered
  2. washwashed with cold ether (100 mL)
  3. dissolutionThe potassium salt was dissolved in H2O (50 mL)
  4. customthe solution was acidified with concentrated HCl to pH=4 in a cold bath
  5. extractionThe solution was extracted with ether
  6. dry with materialthe organic phase was dried (MgSO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-cd736840933d49b08d4e6330be5fe87d
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08841455B2

反応ノート

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