Triphenylphosphine → 4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(2-[4-(2-hydroxyethan-1-oxy)phenyl]ethynyl)-1,1-(ethylenedioxy)cyclohexane

HRID 343566

反応式

HRID 343566 の反応式
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1.[CH:12]1([O:17][C:18]2[CH:19]=[C:20]([C:26]3([C:36]#[CH:37])[CH2:31][CH2:30][C:29]4([O:35][CH2:34][CH2:33][O:32]4)[CH2:28][CH2:27]3)[CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[CH2:16][CH2:15][CH2:14][CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>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>[CH:12]1([O:17][C:18]2[CH:19]=[C:20]([C:26]3([C:36]#[C:37][C:8]4[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][OH:1])=[CH:6][CH:7]=4)[CH2:31][CH2:30][C:29]4([O:32][CH2:33][CH2:34][O:35]4)[CH2:28][CH2:27]3)[CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[CH2:13][CH2:14][CH2:15][CH2:16]1

参加物

6

反応物 3

HCID 11776TriphenylphosphineHCID 35132082-(4-Iodophenoxy)ethanolHCID 110895964-(3-Cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-ethynylcyclohexane

生成物 1

HCID 541798624-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(2-[4-(2-hydroxyethan-1-oxy)phenyl]ethynyl)-1,1-(ethylenedioxy)cyclohexane

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8082Piperidine溶媒

実験手順

A solution of 4-(2-hydroxyethoxy)phenyl iodide (0.059 g, 0.22 mmol), and 4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-ethynylcyclohexane (0.080 g, 0.22 nmol) in dry piperidine (1 mL) was treated with a mixture of tetrakis(triphenylphosphine)palladium (0.013 g, 0.011 mmol), cuprous iodide (0.0025 g, 0.013 mmol), and triphenylphosphine (crystal), as described above in Example 11. Purification of the crude product by chromatography (silica gel, 1 to 2% methanol in methylene chloride) followed by pumping in vacuo afforded the titled intermediate as a viscous oil. 1H-NMR (400 MHz, CDCl3) δ 7.39 (d, J=9.0 Hz, 2H), 7.24 (d, J=2.1 Hz, 1H), 7.13 (d-d, J=8.3 Hz, J=2.1 Hz, 1H), 6.85 (d, J=8.7, 2H), 6.84 (d, J=8.3 Hz, 1H), 4.81 (p, J=2.0 Hz, 1H), 4.09 (t, J=4.4 Hz, 2H), 4.00 (s, 4H), 3.97 (t, J=4.4 Hz, 2H), 3.84 (s, 3H), 2.3 to 1.5 (m, 21H with H2O).

後処理

  1. customPurification of the crude product by chromatography (silica gel, 1 to 2% methanol in methylene chloride)

出典と根拠

ORDレコード
ord-4b56e8e3b034477b8d9b5cb306c0e014
出典データセット
uspto-grants-1999_01
特許番号
US05861421

関連ノート

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