Water → 4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(4-pyridylethynyl)-1,1-(ethylenedioxy)cyclohexane

HRID 343555

反応式

HRID 343555 の反応式
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:25]#[CH:26])[CH2:20][CH2:19][C:18]4([O:24][CH2:23][CH2:22][O:21]4)[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>N1CCCCC1.[Cu]I>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:25]#[C:26][C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[CH2:20][CH2:19][C:18]4([O:21][CH2:22][CH2:23][O:24]4)[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

7

反応物 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 142684-BromopyridineHCID 110895964-(3-Cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-ethynylcyclohexane

生成物 1

HCID 544017964-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(4-pyridylethynyl)-1,1-(ethylenedioxy)cyclohexane収率 93%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8082Piperidine溶媒

実験手順

To a solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-ethynyl-1,1-(ethylenedioxy)cyclohexane (0.10 g, 0.28 mmol) and 4-bromopyridine (0.54 g, 2.8 mmol) in piperidine (1.5 mL) under an argon atmosphere were added tetrakis(triphenyl-phosphine)palladium(0) (0.013 g, 4%), copper(I) iodide (0.004 g, 6%) and a small crystal of triphenylphosphine, and the mixture was heated at 80°-85° C. for 0.5 h. Water was added, the mixture was extracted three times with dichloromethane, was dried (magnesium sulfate),and was evaporated. Purification by flash chromatography, eluting with 35:65 ethyl acetate:hexanes, provided 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(4-pyridylethynyl)-1,1-(ethylenedioxy)cyclohexane as a pale yellow oil (0.11 g, 93%). 1H-NMR (400 MHz, CDCl3) δ 8.56 (d, J=5.3 Hz, 2H), 7.33 (d, J=5.3 Hz, 2H), 7.16 (d, J=2.2 Hz, 1H), 7.09 (dd, J=8.5, 2.2 Hz, 1H), 6.85 (d, J=8.5 Hz, 1H), 4.80 (m, 1H), 4.00 (m, 4H), 3.85 (s, 3H), 2.0-2.2 (m, 6H), 1.8-2.0 (m, 8H), 1.59 (m, 2H).

後処理

  1. extractionthe mixture was extracted three times with dichloromethane
  2. customwas evaporated
  3. customPurification by flash chromatography
  4. washeluting with 35:65 ethyl acetate

出典と根拠

ORDレコード
ord-e67a5e0fcfe94631ad0adabff978abc1
出典データセット
uspto-grants-1999_01
特許番号
US05861421

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