Cyclohexane ethylacetate → Tert-butyl 3-(3-amino-4-chlorophenyl)propanoate

HRID 1476056ノート

反応式

HRID 1476056 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:4][C:3]=1[N+:17]([O-])=O.C1CCCCC1.C(OCC)(=O)C>[Pd].C(O)C.C1COCC1>[C:13]([O:12][C:10](=[O:11])[CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([NH2:17])[CH:4]=1)([CH3:16])([CH3:14])[CH3:15]

参加物

6

反応物 2

HCID 21867204Cyclohexane ethylacetateHCID 58136394tert-Butyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate

生成物 1

HCID 58136497Tert-butyl 3-(3-amino-4-chlorophenyl)propanoate

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

At room temperature, 500 mg of palladium on carbon (10%) were added to a solution of 6.74 g (23.76 mmol) of tert-butyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate in 200 ml of ethanol and 20 ml of THF, and the mixture was hydrogenated under atmospheric pressure for 12 h. After the reaction had gone to completion (monitored by TLC; mobile phase cyclohexane/ethyl acetate 1:1), the reaction solution was filtered through kieselguhr and the filtrate was concentrated under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 4:1→2:1). This gave 1.40 g (5.47 mmol, 23% of theory) of the title compound.

後処理

  1. filtrationthe reaction solution was filtered through kieselguhr
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 4:1→2:1)

出典と根拠

ORDレコード
ord-867ead1e79c645648e6e96864b8f5a93
出典データセット
uspto-grants-2015_04
特許番号
US09018414B2

反応ノート

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