Water → HCID 69477657, compound

HRID 1295481Notes

Reaction equation

HRID 1295481 reaction equation
[C:1]1([CH:7]2[O:11][CH:10]([CH2:12][CH2:13][CH2:14]O)[C:9](=[C:16]=[CH2:17])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH2:18].[C:19]([O:22][CH2:23][CH3:24])(=[O:21])C>CO.Cl[Pd]Cl>[C:1]1([CH:7]2[O:11][CH:10]3[C:9]([C:16](=[CH2:17])[C:19]([O:22][CH2:23][CH3:24])=[O:21])([O:18][CH2:14][CH2:13][CH2:12]3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 587946423-(3-Ethenylidene-5-phenyloxolan-2-yl)propan-1-ol

Product 1

HCID 69477657HCID 69477657, compound

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 887MethanolSolvent

Procedure

3-(5-phenyl-3-vinylidene-tetrahydrofuran-2-yl)propan-1-ol (66 mg, 0.29 mmol) was dissolved in 2 mL of methanol, and then was filled with CO gas (1 atm), followed by addition of PdCl2 (5.2 mg, 0.029 mmol) and CuCl2 (117 mg, 0.87 mmol). The solution was stirred for 4 hours at room temperature. When the reaction was completed, H2O was added and the solution was stirred for 5 minutes. The mixture was diluted with ethyl acetate, washed with H2O and NaCl. Organic layer was separated and dried with anhydride MgSO4. Solvent was removed under reduced pressure, and the remnant was purified through silica gel tube chromatography (EtOAc:n-Hexane=1:25, v/v), thus providing products (56 mg, 65%).

Workup

  1. additionwas filled with CO gas (1 atm)
  2. stirringthe solution was stirred for 5 minutes
  3. washwashed with H2O and NaCl
  4. customOrganic layer was separated
  5. dry with materialdried with anhydride MgSO4
  6. customSolvent was removed under reduced pressure
  7. customthe remnant was purified through silica gel tube chromatography (EtOAc

Sources & evidence

ORD record
ord-3dacefb2e9c042ac9b776e1f75776c11
Source dataset
uspto-grants-2007_07
Patent number
US07241906B2

Reaction notes

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