3-Butyn-1-OL → 4-(Biphenyl-4-yl)but-3-yn-1-ol

HRID 877419

反応式

HRID 877419 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:14]([OH:18])[CH2:15][C:16]#[CH:17]>CCN(CC)CC.C(Cl)Cl.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>[C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:7][C:2]([C:17]#[C:16][CH2:15][CH2:14][OH:18])=[CH:3][CH:4]=1

参加物

7

反応物 2

HCID 135663-Butyn-1-OLHCID 153224-Iodobiphenyl

生成物 1

HCID 583662084-(Biphenyl-4-yl)but-3-yn-1-ol収率 86.8%

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 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

反応条件

温度
23 °C

実験手順

A sample of 4-iodobiphenyl (400 mg, 1.40 mmol) and (PPh3)4Pd (32 mg, 0.02 mmol) were dissolved in Et3N (6 mL) and stirred at 23° C. for 15 min before CuI (13.5 mg, 0.071 mmol) and but-3-yn-1-ol (0.129 mL, 1.71 mmol) were added. The reaction mixture was stirred at 23° C. for 3 h and then diluted with CH2Cl2, washed with saturated aqueous NH4Cl and saturated aqueous NaCl, and dried over Na2SO4. Evaporation in vacuo yielded the crude product. Flash chromatography (SiO2, 20% EtOAc-hexanes) afforded the title compound (270 mg, 85%) as a white solid: 1H NMR (CDCl3, 500 MHz) δ 7.59 (dd, 2H, J=8.5 Hz), 7.54 (dd, 4H, J=8.5 Hz), 7.44 (t, 2H, J=7.5 Hz), 7.36 (t, 1H, J=7.5 Hz), 3.84 (t, 2H, J=6.5 Hz), 2.73 (t, 2H, J=6.0 Hz); 13C NMR (CDCl3, 125 MHz) δ 140.6, 140.2, 132.0, 128.7, 127.5, 126.9, 126.8, 122.2, 87.0, 82.2, 61.1, 23.9.

後処理

  1. additionwere added
  2. washwashed with saturated aqueous NH4Cl and saturated aqueous NaCl
  3. dry with materialdried over Na2SO4
  4. customEvaporation in vacuo
  5. customyielded the crude product

出典と根拠

ORDレコード
ord-881ba1501aa3465ab0ae87c3d11ade4c
出典データセット
uspto-grants-2015_03
特許番号
US08987312B2

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