Cyclopropanecarbonyl chloride → Ethyl 4-(cyclopropanecarbonyl)benzoate

HRID 713073

反応式

HRID 713073 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([Zn]I)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[CH:14]1([C:17](Cl)=[O:18])[CH2:16][CH2:15]1>C1COCC1.Cl[Pd](Cl)(P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:14]1([C:17]([C:9]2[CH:10]=[CH:11][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=2)=[O:18])[CH2:16][CH2:15]1

参加物

5

反応物 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 178469117HCID 178469117、化合物

生成物 1

HCID 24724092Ethyl 4-(cyclopropanecarbonyl)benzoate収率 78.4%

試薬・触媒・溶媒 2

HCID 178479802HCID 178479802、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

(4-Ethoxycarbonylphenyl)-iodo-zinc (20 mL of 0.5 M in THF, 10.0 mmol) was added over 10 min to dichloro-bis(triphenylphosphoranyl)palladium (211 mg, 0.3 mmol) in THF (20 mL) under an atmosphere of nitrogen at 0° C. The reaction mixture was stirred for 15 minutes, cyclopropanecarbonyl chloride (941 mg, 817 μL, 9.0 mmol) was added dropwise at 0° C. and stirred for 2 hours. The reaction mixture was quenched with 1M HCl (20 mL), extracted with ethyl acetate (2×50 mL). The organic layer was washed sequentially with sat. aq. NaHCO3 (5 mL) and brine solution (50 mL), dried over MgSO4 and purified by silica gel column chromatography using 0-30% EtOAc/hexanes as eluent to give ethyl 4-(cyclopropanecarbonyl)benzoate (1.54 g, 71%) as a pale yellow oil. ESI-MS m/z calc. 218.0. found 219.3 (M+1)+; Retention time: 1.57 minutes (3 min run).

後処理

  1. stirringstirred for 2 hours
  2. customThe reaction mixture was quenched with 1M HCl (20 mL)
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. washThe organic layer was washed sequentially with sat. aq. NaHCO3 (5 mL) and brine solution (50 mL)
  5. dry with materialdried over MgSO4
  6. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-68a84cabc4444674870de6c805b18ff4
出典データセット
uspto-grants-2015_11
特許番号
US09181273B2

関連ノート

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