Methanol → HCID 60155617, compound

HRID 1506885Notes

Reaction equation

HRID 1506885 reaction equation
Br[C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([F:15])[CH:3]=1.[CH3:16][Zn]C.CO>O1CCOCC1.C(OCC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Br[Pd]Br>[F:15][C:4]1[CH:3]=[C:2]([CH3:16])[C:7]([F:8])=[CH:6][C:5]=1[CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11]

Participants

7

Reactant 3

HCID 887MethanolHCID 60155616HCID 60155616, compoundHCID 178477796HCID 178477796, compound

Product 1

HCID 60155617HCID 60155617, compoundYield 144%

Reagents, catalysts & solvents 3

HCID 11104744HCID 11104744, compoundCatalystHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of trans-dibromobis(triphenylphosphine)-palladium(II) [trans-Pd(PPh3)2Br2] (0.048 g, 5.6 mol %) in 1,4-dioxane (30 mL), a solution of compound (30a) (3.0 g, 10.7 mmol) in dry 1,4-dioxane (4 mL) was added under argon gas flow. To this mixture, dimethyl zinc (2M-solution in toluene, 11.0 mL, 22.0 mmol) was slowly added dropwise and the reaction mixture was heated to reflux for 4 hours. After cooling the reaction mixture to room temperature, methanol (4.0 mL) was added to the reaction mixture and the obtained mixture was diluted with diethyl ether. The organic layer was washed with a 1M aqueous solution (34 mL) of hydrochloric acid and dried (over magnesium sulfate). The solvent was distilled off, and the obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (4:1) solution to give 3.3 g (83%) of compound (31a) as colorless liquid matter.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. washThe organic layer was washed with a 1M aqueous solution (34 mL) of hydrochloric acid
  4. dry with materialdried (over magnesium sulfate)
  5. distillationThe solvent was distilled off
  6. washthe obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (4:1) solution

Sources & evidence

ORD record
ord-21b1a374e13e4ffb80a09249d2fa6efe
Source dataset
uspto-grants-2015_12
Patent number
US09221786B2

Reaction notes

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