HCID 22313290, compound → HCID 22313309, compound

HRID 965839Notes

Reaction equation

HRID 965839 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[CH:15]=[CH2:16])[C:8]([O:10][CH3:11])=[O:9])C=C>C(Cl)Cl.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1C=CC(C=[Ru](Cl)Cl)=CC=1>[O:4]1[C:5]2[C:14](=[CH:13][CH:12]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[CH:6]=2)[CH:15]=[CH:16][CH2:1]1

Participants

4

Reactant 1

HCID 22313290HCID 22313290, compound

Product 1

HCID 22313309HCID 22313309, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 11967259Benzylidenebis(tricyclohexylphosphine)dichlororutheniumCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 3-(allyloxy)-4-vinylbenzoate (0.67 g, 3.1 mmol) in CH2Cl2 (20 mL) at rt is added benzylidene-bis(tricyclohexylphosphine)dichlororuthenium (63 mg, 0.076 mmol). The mixture is stirred at rt for 2 h. The reaction mixture is concentrated in vacuo to a dark residue. The crude product is purified by flash chromatography on SiO2. Elution with hexanes-EtOAc (95:5) gives 372 mg (64%) of methyl 2H-chromene-7-carboxylate as a clear oil: 1H NMR (400 MHz, CDCl3) δ 7.56, 7.46, 7.01, 6.46, 5.91, 4.89, 3.91.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo to a dark residue
  2. customThe crude product is purified by flash chromatography on SiO2
  3. washElution with hexanes-EtOAc (95:5)

Sources & evidence

ORD record
ord-e5ea8b4738e942db84c52dd5edad3d2f
Source dataset
uspto-grants-2005_10
Patent number
US06951868B2

Reaction notes

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