Tributylvinyltin → HCID 86675861、化合物

HRID 1427766ノート

反応式

HRID 1427766 の反応式
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]

参加物

5

反応物 2

HCID 81998Tributylvinyltin2 回HCID 2734889(1R)-1-(3-bromophenyl)ethan-1-ol

生成物 1

HCID 86675861HCID 86675861、化合物収率 89%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒2 回HCID 1140Toluene溶媒

反応条件

温度
45 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2473b59140e249b0913a7089a4a6b8dd
出典データセット
uspto-grants-2015_01
特許番号
US08933015B2

反応ノート

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