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

HRID 877219ノート

反応式

HRID 877219 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>[NH2:17][C:3]1[CH:4]=[C:5]([CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:6]=[CH:7][C:2]=1[Cl:1]

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 hours. 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-7d6d03eaa0544af1bc3b5bb2f6562a64
出典データセット
uspto-grants-2015_03
特許番号
US08987256B2

反応ノート

読み込み中…