Acetic Acid → HCID 69458241, compound

HRID 852409Notes

Reaction equation

HRID 852409 reaction equation
[Li][CH2:2]CCC.[F:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:8]=1[C:15]1([CH3:20])[O:19]CCO1.IC.C(O)(=O)C>C1COCC1.CCOCC>[F:6][C:7]1[C:12]([CH3:2])=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:8]=1[C:15](=[O:19])[CH3:20]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 22615139HCID 22615139, compoundHCID 178418339Butyllithium

Product 1

HCID 69458241HCID 69458241, compoundYield 43.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

17.69 ml (1.6 M in n-hexane, 28.30 mmol) n-BuLi were added slowly to a cooled solution (−78° C.) of the above prepared 4.29 g (20.21 mmol) 2-(2-fluoro-4-methoxy-phenyl)-2-methyl-[1,3]-dioxolane in 100 ml THF. The reaction was stirred for 30 min at this temperature. 5.03 ml (80.86 mmol) of iodomethane were then added over 20 min and after 6 h at −78° C. the reaction was stopped with 3.24 ml (56.60 mmol) of acetic acid in 5 ml ether. The reaction mixture was taken up in ether and washed with aqueous 10% KHSO4 solution and aqueous 10% NaCl solution. The water phases were extracted with ether (two times). The organic phase was dried (Na2SO4) and evaporated. The crude product was dissolved in 30 ml dioxane and treated slowly with 6.74 ml of aqueous 6M HCl. After 2 h, the reaction was taken up in ether and washed with aqueous 10% NaCl solution (two times). The water phases were extracted with ether (two times). The organic phase was dried (Na2SO4), evaporated and purified by flash chromatography (SiO2; n-heptane/CH2Cl2=4:1) to give 1.60 g of the title compound.

Workup

  1. washwashed with aqueous 10% KHSO4 solution and aqueous 10% NaCl solution
  2. extractionThe water phases were extracted with ether (two times)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated
  5. dissolutionThe crude product was dissolved in 30 ml dioxane
  6. additiontreated slowly with 6.74 ml of aqueous 6M HCl
  7. waitAfter 2 h
  8. washwashed with aqueous 10% NaCl solution (two times)
  9. extractionThe water phases were extracted with ether (two times)
  10. dry with materialThe organic phase was dried (Na2SO4)
  11. customevaporated
  12. custompurified by flash chromatography (SiO2; n-heptane/CH2Cl2=4:1)

Sources & evidence

ORD record
ord-ef3175b931cd41db8194150587791a6d
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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