2-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid → 2-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)-benzoic acid 2-propenyl ester

HRID 490041

반응식

HRID 490041 반응식
Br[CH:2]=[CH:3][CH3:4].[CH:5]1[CH:6]=[CH:7][C:8]([C:27]([OH:29])=[O:28])=[C:9]([C:11]2[C:21]3[CH:22]=[CH:23][C:24]([OH:26])=[CH:25][C:20]=3[O:19][C:18]3[C:12]=2[CH:13]=[CH:14][C:15]([CH:17]=3)=[O:16])[CH:10]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:4]([O:29][C:27](=[O:28])[C:8]1[CH:7]=[CH:6][CH:5]=[CH:10][C:9]=1[C:11]1[C:12]2[C:18]([O:19][C:20]3[C:21]=1[CH:22]=[CH:23][C:24](=[O:26])[CH:25]=3)=[CH:17][C:15]([OH:16])=[CH:14][CH:13]=2)[CH:3]=[CH2:2]

참가 물질

5

반응물 3

HCID 33832-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acidHCID 11430Potassium CarbonateHCID 115331-Bromo-1-propene

생성물 1

HCID 576736762-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)-benzoic acid 2-propenyl ester수율 21%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
65 °C

실험 절차

Bromo-1-propene (0.78 mL, 9.0 mmol) was added dropwise under argon to a stirred mixture of fluorescein 16 (3.0 g, 9.0 mmol) and K2CO3 (1.24 g, 9.0 mmol) in dry DMF (40 mL). The resulting mixture was stirred for 4 h at 65° C. The mixture was concentrated, diluted with ethyl acetate, washed with 10% NaHCO3, brine, dried with anhydrous Na2SO4, and evaporated. The residue was purified by column chromatography (ethyl acetate/hexane=2:1) to give 21 as a brown solid (0.70 g, 21%). 1H NMR (CDCl3, 500 MHz) δ 4.42 (d, J=6.0 Hz, 2H, CH2), 5.06 (m, 2H, 2CH), 5.53 (m, 1H, CH), 6.81 (m, 2H), 6.88 (m, 2H), 6.98 (m, 2H), 7.32 (d, J=7.5 Hz, 1H), 7.68 (t, J=7.5 Hz, 1H), 7.74 (t, J=7.5 Hz, 1H), 8.26 (d, J=7.5 Hz, 1H). 13C NMR (CDCl3, 125 MHz) δ 66.26, 103.90, 115.01, 119.49, 122.30, 130.02, 130.51, 130.65, 131.00, 131.38, 132.77, 134.48, 155.89, 158.06, 165.08, 175.84. ESIMS calcd for C23H17O5 [M+H]+ 373.1. Found 373.2.

후처리

  1. concentrationThe mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with 10% NaHCO3, brine
  4. dry with materialdried with anhydrous Na2SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography (ethyl acetate/hexane=2:1)

출처 및 근거

ORD 기록
ord-c82529e4e01e4a7cacafbd61d0d38fdb
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07527934B2

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