Furan → HCID 21350305、化合物

HRID 1264217ノート

反応式

HRID 1264217 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH3:6][O:7][C:8](=[O:19])[C:9]([C:12]1[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=1)([CH3:11])[CH3:10]>CN(CCN(C)C)C.C1COCC1.CCOCC.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>[CH3:6][O:7][C:8](=[O:19])[C:9]([C:12]1[CH:13]=[CH:14][C:15]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:16][CH:17]=1)([CH3:11])[CH3:10]

参加物

6

反応物 2

HCID 8029FuranHCID 3651431Methyl 2-(4-bromophenyl)-2-methylpropanoate

生成物 1

HCID 21350305HCID 21350305、化合物収率 89.8%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 3283Diethyl Ether溶媒HCID 86588997Thf tmeda溶媒

反応条件

温度
60 °C

実験手順

To a cooled (0° C.) solution of furan (5.7 mL, 78 mmol) in TMEDA/THF (81.4 mL, 14/86) is added n-buLi (15 mL, 2.5 M in hexanes). The cold bath is removed and the resulting solution stirred for 45 minutes, then a solution of ZnCl2 in THF added (40 mL, 0.5M). To this solution is added (Ph3P)4Pd (1.0 g, 0.86 mmol) and 2-(4-Bromo-phenyl)-2-methyl-propionic acid methyl ester (4.5 g, 17.5 mmol) (reference example 31 a). The resulting solution is warmed to 60° C. and stirred for 3 hours. The reaction mixture is then cooled, diluted with ether, washed with hydrochloric acid (2M), then brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 5% ether in hexanes) to give 3.84 g of the title compound as a solid. 1H NMR (CDCl3) d 1.60 (s, 6H), 3.67 (s, 3H), 6.45 (m, 1H), 6.63 (d, J=3 Hz, 1H), 7.35 (m, 2H), 7.46 (m, 1H), 7.65 (m, 2H). MS (EI) m/z 245 (M+H)+.

後処理

  1. customThe cold bath is removed
  2. additiona solution of ZnCl2 in THF added (40 mL, 0.5M)
  3. stirringstirred for 3 hours
  4. temperatureThe reaction mixture is then cooled
  5. washwashed with hydrochloric acid (2M)
  6. dry with materialbrine, dried over MgSO4
  7. concentrationconcentrated
  8. customThe residue is purified by flash chromatography (eluting with 5% ether in hexanes)

出典と根拠

ORDレコード
ord-0c9442a1e99e4fa0a0b730d98361d905
出典データセット
uspto-grants-2003_04
特許番号
US06541505B1

反応ノート

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