Tributylstannane → Methyl 3-(2,4-dimethoxy-5-methylphenyl)octanoate

HRID 1418211Notes

Reaction equation

HRID 1418211 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([CH:11]2SCCCS2)=[CH:5][C:4]=1[CH:17]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:18][C:19]([O:21][CH3:22])=[O:20].C([SnH](CCCC)CCCC)CCC.CCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([CH3:11])=[CH:5][C:4]=1[CH:17]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:18][C:19]([O:21][CH3:22])=[O:20]

Participants

7

Reactant 4

HCID 5948TributylstannaneHCID 8058HexaneHCID 8857Ethyl AcetateHCID 19348574Methyl 3-[2,4-dimethoxy-5-(1,3-dithian-2-yl)phenyl]octanoate

Product 1

HCID 19348590Methyl 3-(2,4-dimethoxy-5-methylphenyl)octanoateYield 92.5%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 558 mg (1.35 mmol) of methyl 3-[2,4-dimethoxy-5-(1,3-dithian-2-yl)phenyl]octanoate [prepared as described in step (i) above], 1.576 g (5.42 mmol) of tributyltin hydride and 15 mg of azobis(isobutyronitrile) in 20 ml of toluene was stirred whilst heating at 100° C. for 6.5 hours. At the end of this time, the reaction temperature was allowed to reduce to room temperature, and the reaction mixture was purified by column chromatography through 15 g of silica gel, using a gradient elution method, with mixtures of hexane and ethyl acetate ranging from 6:0 to 6:1 by volume as the eluent, to give a mixture containing the reduced product. The mixture was further purified by column chromatography through 30 g of alumina, using a gradient elution method, with mixtures of hexane and ethyl acetate ranging from 20:0 to 20:1 by volume as the eluent, to give 385 mg (yield 92%) of methyl 3-(2,4-dimethoxy-5-methylphenyl)octanoate as an oily substance.

Workup

  1. customto reduce to room temperature
  2. customthe reaction mixture was purified by column chromatography through 15 g of silica gel
  3. washa gradient elution method
  4. customwith mixtures of hexane and ethyl acetate ranging from 6:0 to 6:1 by volume as the eluent, to give a mixture
  5. additioncontaining the reduced product
  6. customThe mixture was further purified by column chromatography through 30 g of alumina
  7. washa gradient elution method

Sources & evidence

ORD record
ord-4ba853a3bb304611827397a000b67d46
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

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