Water → HCID 131734282, 화합물

HRID 1501525노트

반응식

HRID 1501525 반응식
[CH3:1][O:2][C:3]1[C:4]([O:15][CH3:16])=[CH:5][C:6]2[O:10][C:9]([C:11](=[O:13])[CH3:12])=[CH:8][C:7]=2[CH:14]=1.C(O[K])(C)(C)C.[CH2:23](Br)/[CH:24]=[C:25](/[CH2:27][CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31])\[CH3:26].O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]([O:15][CH3:16])=[CH:5][C:6]2[O:10][C:9]([C:11](=[O:13])[CH2:12][CH2:23][CH:24]=[C:25]([CH3:26])[CH2:27][CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31])=[CH:8][C:7]=2[CH:14]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 176913Caleprunin BHCID 53658672,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-HCID 178418922HCID 178418922, 화합물

생성물 1

HCID 131734282HCID 131734282, 화합물

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 1-(5,6 dimethoxy benzofuran-2-yl)ethanone A2 (1 g, 4.545 mmol) in anhydrous Toluene added tBuOK (0.51 g, 4.545 mmol) at 0° C. under argon atmosphere and then stirred at the same temperature for 15 min to this reaction mixture geranyl bromide added drop wise. Resulting suspension stirred at the same temperature for 2 hrs. 50 ml water was added to the reaction mixture and layers were separated. Aqueous layer was extracted with ethylaectate. The combined organic extract were washed with brine and dried over Na2SO4, evaporated under reduced pressure. Chromatography of the residue on silica gel (5% EtOAc/hexanes) afforded the ketone A3 (1.69 g) in 70% yield pale yellow liquid: 1H NMR (500 MHz, CDCl3) δ 7.425 (s, 1H), 7.365 (s, 1H), 7.06 (s, 1H), 5.12-5.16 (m, 1H), 5.08-5.04 (m, 1H), 3.96 (s, 3H), 3.93 (s, 3H), 2.97-2.89 (t, 2H), 2.50-2.40 (m, 2H), 2.17-2.00 (m, 4H), 1.66 (s, 3H), 1.63 (s, 3H), 1.64 (s, 3H), 1.58 (s, 3H), ppm. Mass: ESI [M+Na]+: 379.2; Elemental anal. calcd. for C22H28O4; C, 74.13; H, 7.92. found C, 74.0; H, 5.25.

후처리

  1. customResulting suspension
  2. customwere separated
  3. extractionAqueous layer was extracted with ethylaectate
  4. extractionThe combined organic extract
  5. washwere washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-1ae505cc8f6243689c5d22e4434b7395
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206201B2

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