Boron trifluoride etherate → Methyl 3-[2,4-dimethoxy-5-(1,3-dithian-2-yl)phenyl]octanoate

HRID 1418210노트

반응식

HRID 1418210 반응식
[CH2:1]([SH:5])[CH2:2][CH2:3][SH:4].S([O-])([O-])(=O)=O.[Mg+2].B(F)(F)F.CCOCC.[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[C:26]([CH:31]=O)=[CH:25][C:24]=1[CH:33]([CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:34][C:35]([O:37][CH3:38])=[O:36].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[C:26]([CH:31]2[S:5][CH2:1][CH2:2][CH2:3][S:4]2)=[CH:25][C:24]=1[CH:33]([CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:34][C:35]([O:37][CH3:38])=[O:36]

참가 물질

7

반응물 5

HCID 8000Boron trifluoride etherateHCID 80131,3-PropanedithiolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 19348477Methyl 3-(2,4-dimethoxy-5-formylphenyl)octanoate

생성물 1

HCID 19348574Methyl 3-[2,4-dimethoxy-5-(1,3-dithian-2-yl)phenyl]octanoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

150 mg (1.39 mmol) of 1,3-propanedithiol, 1.0 g of magnesium sulfate and a catalytic amount of boron trifluoride etherate were added, with ice-cooling, to a solution of 447 mg (1.39 mmol) of methyl 3-(2,4-dimethoxy-5-formylphenyl)-octanoate [prepared as described in Preparation 32(ii)] in 12 ml of methylene chloride, and the resulting mixture was stirred at the same temperature for 2 hours. At the end of this time, the reaction mixture was neutralized with a saturated aqueous solution of sodium hydrogencarbonate, and then the dehydrating agent was removed by filtration using a Celite (trade mark) filter aid. The filtrate was concentrated by evaporation under reduced pressure, and the concentrate was extracted with ethyl acetate. The extract was washed with water and with a saturated aqueous solution of sodium chloride, in that order, after is which it was dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 10 g of silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 589 mg (a quantitative yield) of the 1,3-dithiane derivative as an oily substance.

후처리

  1. customthe dehydrating agent was removed by filtration
  2. filtrationfilter aid
  3. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  4. extractionthe concentrate was extracted with ethyl acetate
  5. washThe extract was washed with water and with a saturated aqueous solution of sodium chloride, in that order
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customthe resulting residue was purified by column chromatography through 10 g of silica gel
  9. additionby volume mixture of hexane and ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-ff3f82eb49114703baf0a2f53ed96b3e
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05880147

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