Furan → HCID 21350305, 화합물

HRID 1264217노트

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HRID 1264217 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

HCID 21350305HCID 21350305, 화합물수율 89.8%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 3283Diethyl Ether용매HCID 86588997Thf tmeda용매

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온도
60 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-0c9442a1e99e4fa0a0b730d98361d905
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06541505B1

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