Ethyl (2Z)-3-cyanoprop-2-enoate → HCID 21923192, 화합물

HRID 1244844

반응식

HRID 1244844 반응식
[C:1]1([C:6]2[NH:7][C:8]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:5][CH2:4][CH2:3][CH:2]=1.[C:15](/[CH:17]=[CH:18]\[C:19]([O:21][CH2:22][CH3:23])=[O:20])#[N:16]>CCOCC>[C:15]([CH:17]1[CH:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[C:1]2[CH2:5][CH2:4][CH2:3][C:2]1=2)#[N:16]

참가 물질

4

반응물 2

HCID 15577688Ethyl (2Z)-3-cyanoprop-2-enoateHCID 21923221HCID 21923221, 화합물

생성물 1

HCID 21923192HCID 21923192, 화합물수율 8.3%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

2-(Cyclopenten-1-yl)indole (13.6 g, 74 mmol), ethyl cis-3-cyanoacrylate (17.8 g, 142 mmol) and BHT (70 mg) were heated to 180° C. under nitrogen for 30 min. The volatiles were removed by kugelrohr distillation at 110° C. and 0.8 mm to afford 19.7 g of an amber-brown tar. Addition of ether (50 mL) afforded a precipitate of a single isomer of white crystalline ethyl 4-cyano-1,2,3,4,5,10-hexahydrocyclopenta[a]carbazole-5-carboxylate (1.89 g, 8.2% yield); mp 192–195° C. NMR (CDCl3) δ 7.91 (s, 1H), 7.46 (d, 1H), 7.34 (d, 1H), 7.12 (m, 2H), 4.31 (d, 1H0, 4.32 (m, 2H), 4.20 (d, 1H), 3.46 (t, 1H), 3.30 (q, 1H), 2.80 (m, 1H), 2.3–1.4 (m, 6H), 1.34 (t, 3H). Anal. Calcd for C19H20N2O2: C, 74.00; H, 6.54; N, 9.08. Found: C, 73.84; H, 6.53; N, 9.03.

후처리

  1. customThe volatiles were removed by kugelrohr distillation at 110° C.
  2. custom0.8 mm to afford 19.7 g of an amber-brown tar

출처 및 근거

ORD 기록
ord-25f5c61453e34c818d295fa24b5926d2
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07122679B2

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