Carbon Tetrachloride → 1-(2-Chloroethyl)-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole

HRID 901058노트

반응식

HRID 901058 반응식
[CH2:1]([C:3]1([CH2:18][CH2:19]O)[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:16][CH3:17])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)(Cl)(Cl)[Cl:41]>O>[Cl:41][CH2:19][CH2:18][C:3]1([CH2:1][CH3:2])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:16][CH3:17]

참가 물질

5

반응물 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 108910512-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-ethanol

생성물 1

HCID 219075721-(2-Chloroethyl)-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole수율 51%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of compound 1 (136 mg, 0.5 mmol), PPh3 (262 mg, 1.0 mmol, 2.0 eq), and CCl4 (2.5 mL) was refluxed overnight. The resulting mixture was then diluted with water and extracted three times with CH2Cl2. The organic phases were combined, dried with Na2SO4, concentrated, and purified by column chromatography using 5:95:EtOAc:Hexane to give a white solid (74 mg, 51%): mp 106-107° C. (dec). 1HNMR (CDCl3, δ TMS): 0.93 (t, 3H), 1.37 (t, 3H), 1.91 (m, 2H), 2.34 (m, 2H), 2.76 (m, 2H), 2.87 (q, 2H), 3.46 (dm, 2H), 3.99 (m, 2H), 7.04-7.38 (m, 3H, Ar—H), 7.55 (br, 1H, NH). MS−: m/z 326 (MCl−), 290 ([M−H]−). Anal. (C17H22NOCl): C, H, N.

후처리

  1. extractionextracted three times with CH2Cl2
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated
  4. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-93f84b78654546f988253242b342eb3d
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361680B2

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