Lithium acetate → HCID 86629263, compound

HRID 1868949Notes

Reaction equation

HRID 1868949 reaction equation
[Cl:1][C:2]1[C:3]([C:19]#[C:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:4]([C:8]2([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C([O-])(=[O:28])C.[Li+]>C(O)(C(F)(F)F)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[C:3](/[C:19](/[OH:28])=[CH:20]/[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:4]([C:8]2([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3474584Lithium acetateHCID 67099918HCID 67099918, compound

Product 1

HCID 86629263HCID 86629263, compoundYield 39.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of ethyl 4-(3-chloro-2-(3-ethoxy-3-oxoprop-1-ynyl)phenyl)-tetrahydro-2H-pyran-4-carboxylate (0.5 g, 1 mmol) in 1.5 mL TFA was stirred at room temperature and treated with lithium acetate (0.09 g, 1 mmol) and palladium(II) acetate (0.02 g, 0.07 mmol). The resulting solution was stirred at room temperature for 2 hours and concentrated. The residue was diluted with 100 mL EtOAc, washed with water (3×20 mL), 20 mL saturated NaCl, dried over anhydrous sodium sulfate, and concentrated. The concentrate was purified by column chromatography (10-20% EtOAc/hexane) to give 0.15 g of the product as a yellow oil. MS m/e: (M+H)+ 383.

Workup

  1. stirringThe resulting solution was stirred at room temperature for 2 hours
  2. concentrationconcentrated
  3. additionThe residue was diluted with 100 mL EtOAc
  4. washwashed with water (3×20 mL), 20 mL saturated NaCl
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by column chromatography (10-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-de37060fdbac454ea10f8c379ce3188b
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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