Tributylvinyltin → HCID 86675861, 화합물

HRID 1427766노트

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HRID 1427766 반응식
Br[C:2]1[CH:3]=[C:4]([C@H:8]([OH:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH2:11]([Sn](CCCC)(CCCC)C=C)[CH2:12]CC>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:11]([C:2]1[CH:3]=[C:4]([C@H:8]([OH:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1)=[CH2:12]

참가 물질

5

반응물 2

HCID 81998Tributylvinyltin2회HCID 2734889(1R)-1-(3-bromophenyl)ethan-1-ol

생성물 1

HCID 86675861HCID 86675861, 화합물수율 89%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매2회HCID 1140Toluene용매

반응 조건

온도
45 °C

실험 절차

Bis(triphenylphosphine)palladium(II) dichloride (360 mg, 0.512 mmol) was added to a degassed solution of (R)-1-(3-bromo-phenyl)-ethanol (1.03 g, 5.123 mmol) and tributyl(vinyl)tin (1.8 ml, 6.15 mmol) in toluene (10 ml) under N2 and the reaction was stirred at 45° C. for 18 h. Tributyl(vinyl)tin (2.56 mmol, 750 uL) and bis(triphenylphosphine)palladium(II) dichloride (0.256 mmol, 180 mg) were added and stirring was continued for 18 h. The reaction was cooled and the solvent evaporated to afford a residue which was absorbed onto SiO2. Purification by SiO2 (3:11-hexane/ethyl acetate) afforded 13a as a yellow oil (675 mg, 89%). 1H NMR (300 MHz, CDCl3) δ7.49 (1H, s), 7.33 (3H, m), 6.75 (1H, dd, J=17.6, 10.9 Hz), 5.80 (1H, d, J=17.6 Hz), 5.28 (1H, d, J=10.7 Hz), 4.93 (1H, m), 1.81 (1H, d, J=3.1 Hz), 1.52 (3H, d, J=6.5 Hz).

후처리

  1. stirringstirring
  2. waitwas continued for 18 h
  3. temperatureThe reaction was cooled
  4. customthe solvent evaporated
  5. customto afford a residue which
  6. customwas absorbed onto SiO2
  7. customPurification by SiO2 (3:11-hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-2473b59140e249b0913a7089a4a6b8dd
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933015B2

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