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

HRID 1160293노트

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HRID 1160293 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-90dce07b42ea4193b3bf5521fc313997
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816367B2

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