Triethylamine → (E)-2-(3,3-Diethoxyprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 17194

반응식

HRID 17194 반응식
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[C:5]#[CH:6])[CH3:2].[CH3:10][C:11]1([CH3:18])[C:15]([CH3:17])([CH3:16])[O:14][BH:13][O:12]1.C(N(CC)CC)C>O1CCCC1.[H-].[Cl-].C1([Zr+2]C2C=CC=C2)C=CC=C1>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])/[CH:5]=[CH:6]/[B:13]1[O:14][C:15]([CH3:17])([CH3:16])[C:11]([CH3:18])([CH3:10])[O:12]1)[CH3:2]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 662853,3-DiethoxypropyneHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolane

생성물 1

HCID 11065022(E)-2-(3,3-Diethoxyprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane수율 53%

시약·촉매·용매 2

HCID 178420592HCID 178420592, 화합물촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

A mixture of 3,3-diethoxy-1-propyne (18.5 g, 0.144 mol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (27.6 g, 0.216 mol) and bis(cyclopentadienyl)zirconium chloride hydride (1.9 g, 0.007 mol) in tetrahydrofuran (75 mL) was heated at 50° C. for 2 days. Triethylamine (2 mL) was added and the solvent was removed in vacuo. The residue was distilled at 90° C. at 10 torr. The residue was purified by column chromatography on neutral alumina using 89:10:1 dichloromethane: ethyl acetate: triethylamine as an eluent. The solvent was removed in vacuo to give the title compound (15.9 g, 53%) as a brown oil. 1H NMR (DMSO-d6, 400 MHz) δ 6.48 (dd, 1H), 5.75 (d, 1H), 4.85 (d, 1H), 3.55-3.67 (m, 2H), 3.40-3.52 (m, 2H), 1.22 (s, 12H), 1.17 (t, 6H).

후처리

  1. customthe solvent was removed in vacuo
  2. distillationThe residue was distilled at 90° C. at 10 torr
  3. customThe residue was purified by column chromatography on neutral alumina using 89:10:1 dichloromethane
  4. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-45b276a754ff450c806d14b42c192eab
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737160B2

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