Methanol → HCID 49837496, compound

HRID 1506869Notes

Reaction equation

HRID 1506869 reaction equation
[F:1][C:2]1[CH:7]=[C:6](OS(C(F)(F)F)(=O)=O)[CH:5]=[CH:4][C:3]=1[CH:16]([CH3:21])[C:17]([O:19][CH3:20])=[O:18].[CH3:22][Zn]C.CO.CCOCC>O1CCOCC1>[F:1][C:2]1[CH:7]=[C:6]([CH3:22])[CH:5]=[CH:4][C:3]=1[CH:16]([CH3:21])[C:17]([O:19][CH3:20])=[O:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 60155357HCID 60155357, compoundHCID 178477796HCID 178477796, compound

Product 1

HCID 49837496HCID 49837496, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a suspension of [1,2-bis(diphenylphospino)ethane]-dichloropalladium(II) [Pd(dppe)Cl2] (14.1 mg and 1.3 mol %) in dry 1,4-dioxane (3 mL), a solution of compound (18) (0.62 g, 1.9 mmol) in dry 1,4-dioxane (3 mL) was added dropwise under argon gas flow. To this suspension, dimethyl zinc (2M-solution in toluene, 9.0 mL, 2.0 mmol) was slowly added dropwise. After completion of the dropwise addition, the suspension was heated to reflux for 4 hours. After cooling, methanol (0.4 mL) was added thereto and the mixture was treated with ether. The organic layer was washed with a 1M aqueous solution (18 mL) of hydrochloric acid and dried (over sodium sulfate), and the solvent was distilled off. The obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (10:1) solution to give 0.26 g (70%) of compound (19) of interest as colorless liquid matter.

Workup

  1. additionAfter completion of the dropwise addition
  2. temperaturethe suspension was heated
  3. temperatureto reflux for 4 hours
  4. temperatureAfter cooling
  5. washThe organic layer was washed with a 1M aqueous solution (18 mL) of hydrochloric acid
  6. dry with materialdried (over sodium sulfate)
  7. distillationthe solvent was distilled off
  8. washThe obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (10:1) solution

Sources & evidence

ORD record
ord-5e50b79b96214d289c42a6f9168ec006
Source dataset
uspto-grants-2015_12
Patent number
US09221786B2

Reaction notes

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