HCID 10192985、化合物 → HCID 10308259、化合物

HRID 1794483ノート

反応式

HRID 1794483 の反応式
[CH2:1]([Li])CCC.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH2:25]O)[C:11]2[O:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[CH:13][C:12]=2[CH:24]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:25]=[CH2:1])[C:11]2[O:15][C:14]([C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)=[CH:13][C:12]=2[CH:24]=1

参加物

5

反応物 2

HCID 10192985HCID 10192985、化合物HCID 178418339Butyllithium

生成物 1

HCID 10308259HCID 10308259、化合物収率 71%

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Methyl triphenylphosphonium bromide (0.122 g, 0.334 mmole) was dissolved in 5 mL THF and placed in an acetone/dry ice bath at −78° C.; n-Butyl lithium (0.131 mL, 0.328 mmole) was added and the mixture was allowed to stir for 30 minutes. To this solution was added aldehyde 3 (0.078 g, 0.278 mmole) in 3 mL THF. After stirring at room temperature for 4 hours, the reaction mixture was placed in an oil bath and allowed to stir overnight. at 65° C. The solvent was evaporated and the residue was poured into water and extracted with ethyl acetate. The combined organic phases were washed with saturated sodium bicarbonate, water, brine, and dried with magnesium sulfate. The organic phases were concentrated and the residue was loaded on to silica gel and chromatographed with silica gel (hexanes:ethyl acetate, 95:5) to afford 0.055 g (71%) of 28 as a white solid: Mp=182–184° C.; 1H NMR (DMSO-d6) δ 7.87 (d, 2 H, J=8.4 Hz), 7.22 (s, 1 H), 7.08 (m, 3 H), 6.98 (m, 1 H), 6.96 (d, 1 H, J=2.3 Hz), 6.30 (d, 1 H, J=17.8 Hz), 5.59 (d, 1 H, J=11.4 Hz), 3.82 (s, 3 H), 3.80 (s, 3 H); MS 281 (M+H)+

後処理

  1. customplaced in an acetone/dry ice bath at −78° C.
  2. stirringAfter stirring at room temperature for 4 hours
  3. customthe reaction mixture was placed in an oil bath
  4. stirringto stir overnight
  5. customat 65° C
  6. customThe solvent was evaporated
  7. additionthe residue was poured into water
  8. extractionextracted with ethyl acetate
  9. washThe combined organic phases were washed with saturated sodium bicarbonate, water, brine
  10. dry with materialdried with magnesium sulfate
  11. concentrationThe organic phases were concentrated
  12. customchromatographed with silica gel (hexanes:ethyl acetate, 95:5)

出典と根拠

ORDレコード
ord-fa99a722b14c4e9196661f70c4815003
出典データセット
uspto-grants-2006_04
特許番号
US07022733B2

反応ノート

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