Ammonium Chloride → 2,2-Dimethyl-5-{1-[4-(2-methyl-benzylsulfanyl)-phenyl]-but-2-ynyl}-[1,3]dioxane-4,6-dione

HRID 1160293ノート

反応式

HRID 1160293 の反応式
[C:1]([Mg]Br)#[C:2][CH3:3].[CH3:6][C:7]1([CH3:31])[O:12][C:11](=[O:13])[C:10](=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([S:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])=[CH:17][CH:16]=2)[C:9](=[O:30])[O:8]1.[NH4+].[Cl-]>C1COCC1>[CH3:6][C:7]1([CH3:31])[O:12][C:11](=[O:13])[CH:10]([CH:14]([C:15]2[CH:16]=[CH:17][C:18]([S:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])=[CH:19][CH:20]=2)[C:1]#[C:2][CH3:3])[C:9](=[O:30])[O:8]1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 591326082,2-Dimethyl-5-[4-(2-methyl-benzylsulfanyl)-benzylidene]-[1,3]dioxane-4,6-dioneHCID 178419101HCID 178419101、化合物

生成物 1

HCID 591326202,2-Dimethyl-5-{1-[4-(2-methyl-benzylsulfanyl)-phenyl]-but-2-ynyl}-[1,3]dioxane-4,6-dione収率 15%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

An oven-dried 100 mL pear-shaped flask, fitted with an oven-dried stir bar, was charged with a 0.5 M solution of 1-propynyl magnesium bromide in THF (12.5 mL, 6.27 mmol) via cannula. The solution was cooled to 0° C., and then a solution of 28.2 (1.05 g, 2.85 mmol) in anhydrous THF (6 mL) was added over 3 minutes via cannula. The reaction was stirred at 0° C. for 5 minutes and then stirred at room temperature for 1.5 hours. The reaction mixture was poured into saturated NH4Cl(aq) and extracted with ethyl acetate. The combined organic layers were washed with water, followed by brine. The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified via radial chromatography (20% ethyl acetate in hexanes) followed by recrystallization from hot ethyl acetate and hexanes to yield 162 mg (15%) of 2,2-Dimethyl-5-{1-[4-(2-methyl-benzylsulfanyl)-phenyl]-but-2-ynyl}-[1,3]dioxane-4,6-dione (28.3). LC/MSD m/e: 409.1 (M+H).

後処理

  1. customAn oven-dried 100 mL pear-shaped flask, fitted with an oven-dried
  2. stirringThe reaction was stirred at 0° C. for 5 minutes
  3. stirringstirred at room temperature for 1.5 hours
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with water
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified via radial chromatography (20% ethyl acetate in hexanes)
  9. customfollowed by recrystallization from hot ethyl acetate and hexanes

出典と根拠

ORDレコード
ord-90dce07b42ea4193b3bf5521fc313997
出典データセット
uspto-grants-2010_10
特許番号
US07816367B2

反応ノート

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