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

HRID 1637530Notes

Reaction equation

HRID 1637530 reaction equation
[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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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-dimetlioxy-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 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.

Workup

  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 materialafter which it was 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

Sources & evidence

ORD record
ord-797e38a5e5ec4518acac8da11bedf8e9
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

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