Hydrochloric Acid → 4-(3-Cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-(4-nitrophenylethynyl)cyclohexane

HRID 343547

反応式

HRID 343547 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.I[C:28]1[CH:33]=[CH:32][C:31](O)=[C:30]([N+:35]([O-:37])=[O:36])[CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>N1CCCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I.O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:25]#[C:26][C:33]4[CH:32]=[CH:31][C:30]([N+:35]([O-:37])=[O:36])=[CH:29][CH:28]=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

9

反応物 4

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 179373Phenol, 4-iodo-2-nitro-HCID 110895964-(3-Cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-ethynylcyclohexane

生成物 1

HCID 153920294-(3-Cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-(4-nitrophenylethynyl)cyclohexane

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 8082Piperidine溶媒

反応条件

温度
80 °C

実験手順

To a solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-ethynylcyclohexane (0.15 g, 0.42 mmol) and 4-iodonitrophenol (0.11 g, 0.42 mmol) in piperidine (2 mL) under an argon atmosphere were added tetrakis(triphenylphosphine)palladium(0) (0.02 g, 4%), copper(I) iodide (0.005 g, 6%) and a small crystal of triphenylphosphine. After heating at 80° C. for 0.5 h, water and 1N hydrochloric acid were added. The mixture was extracted three times with dichloromethane, the extract was dried (magnesium sulfate) and was evaporated. Purification by flash chromatography, eluting with 2:8 ethyl acetate:hexanes, provided 4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-(4-nitrophenylethynyl)cyclohexane as a red-orange wax. mp 58°-59° C. 1H-NMR (400 MHz, CDCl3) δ 8.18 (d, J=8.7 Hz, 2H), 7.58 (d, J=8.7 Hz, 2H), 7.16 (d, J=2.5 Hz, 1H), 7.12 (dd, J=8.4, 2.5 Hz, 1H), 6.86 (d, J=8.4 Hz, 1H), 4.80 (m, 1H), 4.01 (s, 4H), 3.85 (s, 3H), 1.8-2.3 (m, 14H), 1.6 (m, 2H).

後処理

  1. extractionThe mixture was extracted three times with dichloromethane
  2. dry with materialthe extract was dried (magnesium sulfate)
  3. customwas evaporated
  4. customPurification by flash chromatography
  5. washeluting with 2:8 ethyl acetate

出典と根拠

ORDレコード
ord-3e212648411d465c80336b0a234e540c
出典データセット
uspto-grants-1999_01
特許番号
US05861421

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