Water → HCID 131734282、化合物

HRID 1501525ノート

反応式

HRID 1501525 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 131734282HCID 131734282、化合物

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1ae505cc8f6243689c5d22e4434b7395
出典データセット
uspto-grants-2015_12
特許番号
US09206201B2

反応ノート

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