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

HRID 877419

반응식

HRID 877419 반응식
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

참가 물질

7

반응물 2

HCID 135663-Butyn-1-OLHCID 153224-Iodobiphenyl

생성물 1

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

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

반응 조건

온도
23 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-881ba1501aa3465ab0ae87c3d11ade4c
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987312B2

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