Triphenylphosphine → 4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(2-[3-(3-methyl-[1,2,4]oxadiazole-5-yl)phenyl]ethynyl)cyclohexan-1-one

HRID 343572ノート

反応式

HRID 343572 の反応式
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:22]#[CH:23])[CH2:20][CH2:19][C:18](=[O:21])[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:25]1[CH:26]=[C:27]([C:31]2[O:35][N:34]=[C:33]([CH3:36])[N:32]=2)[CH:28]=[CH:29][CH:30]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(N(CC)CC)C.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:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:22]#[C:23][C:29]4[CH:30]=[CH:25][CH:26]=[C:27]([C:31]5[O:35][N:34]=[C:33]([CH3:36])[N:32]=5)[CH:28]=4)[CH2:16][CH2:17][C:18](=[O:21])[CH2:19][CH2:20]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

6

反応物 3

HCID 11776TriphenylphosphineHCID 108289304-(3-Cyclopentyloxy-4-methoxyphenyl)-4-ethynylcyclohexan-1-oneHCID 193499795-(3-Iodophenyl)-3-methyl-1,2,4-oxadiazole

生成物 1

HCID 538356234-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(2-[3-(3-methyl-[1,2,4]oxadiazole-5-yl)phenyl]ethynyl)cyclohexan-1-one収率 78%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8471Triethylamine溶媒

実験手順

A stirred mixture of 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-ethynylcyclohexan-1-one (0.200 g, 0.64 mmol) and 5-(3-iodophenyl)-3-methyl-[1,2,4]oxadiazole (0.201 g, 0.70 mmol) in dry triethylamine (4.6 mL) was treated under argon with a mixture of tetrakis(triphenylphosphine)palladium (0.032 g, 0.028 mmol), cuprous iodide (0.0067 g, 0.035 mmol), and triphenylphosphine (a small crystal) at 70° C. for 1 h and at 25° C. for 15 h. The reaction mixture was concentrated in vacuo and a solution of the residue was dissolved in methylene chloride, was treated with cold dilute hydrochloric acid and was dried over anhydrous sodium sulfate. The crude product was chromatographed (silica, 5 to 10% ethyl acetate in methylene chloride/hexanes 1:1) and the pure fractions were combined, concentrated in vacuo, crystallized from ethyl ether and dried at 60° C. in vacuo to afford the titled compound as an off-white powder (0.235 g, 78%), mp 88°-91° C. Anal. (C29H30N2O4) calcd: C 74.02, H 6.43, N 5.95, found: C 73.77, H 6.53, N 5.78.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiona solution of the residue was dissolved in methylene chloride
  3. additionwas treated with cold dilute hydrochloric acid
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe crude product was chromatographed (silica, 5 to 10% ethyl acetate in methylene chloride/hexanes 1:1)
  6. concentrationconcentrated in vacuo
  7. customcrystallized from ethyl ether
  8. customdried at 60° C. in vacuo

出典と根拠

ORDレコード
ord-38fd0a7e9fce4c91934b860701c3df4e
出典データセット
uspto-grants-1999_01
特許番号
US05861421

反応ノート

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