Water → HCID 68601375, compound

HRID 1951981Notes

Reaction equation

HRID 1951981 reaction equation
[CH2:1]([Li])CCC.C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:26][O:27][C:28]1[CH:35]=[C:34]([O:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH3:42])[CH:33]=[CH:32][C:29]=1[CH:30]=O.O>O1CCCC1>[CH3:26][O:27][C:28]1[CH:35]=[C:34]([O:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH3:42])[CH:33]=[CH:32][C:29]=1[CH:30]=[CH2:1]

Participants

6

Reactant 4

HCID 962WaterHCID 74506TriphenylmethylphosphoniumHCID 86642400HCID 86642400, compoundHCID 178418339Butyllithium

Product 1

HCID 68601375HCID 68601375, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

12.5 ml (31.2 mmol) of n-butyllithium is added dropwise to a solution at −40° C. of 11.1 g (31.2 mmol) of methyl-triphenyl-phosphonium diluted in 100 ml of tetrahydrofuran. The reaction mixture is stirred at 0° C. for 30 minutes and then cooled to −25° C. and a solution of 5 g (20.8 mmol) of 2-methoxy-4-(2-methoxy-ethoxymethoxy)-benzaldehyde diluted in 50 ml of tetrahydrofuran is added dropwise. The reaction mixture is stirred at room temperature for 2 hours. The reaction mixture is treated by adding water and then extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered, and evaporated. The raw product is purified by silica column chromatography, eluted with a heptane/ethyl acetate mixture 75/25 to give 4.4 g (90%) of 2-methoxy-4-(2-methoxy-ethoxymethoxy)-1-vinyl-benzene in the form of a colorless oil.

Workup

  1. temperaturecooled to −25° C.
  2. additionis added dropwise
  3. stirringThe reaction mixture is stirred at room temperature for 2 hours
  4. additionThe reaction mixture is treated
  5. extractionextracted with ethyl acetate
  6. washwashed with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe raw product is purified by silica column chromatography
  11. washeluted with a heptane/ethyl acetate mixture 75/25

Sources & evidence

ORD record
ord-349da44b1cd146a9a1002f9dd7e3cda3
Source dataset
uspto-grants-2013_03
Patent number
US08404836B2

Reaction notes

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