HCID 22313426, compound → HCID 22313331, compound

HRID 965845Notes

Reaction equation

HRID 965845 reaction equation
C([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH:14]([CH3:17])[CH:15]=[CH2:16])[C:6]([O:8][CH3:9])=[O:7])=O>C(Cl)Cl.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1C=CC(C=[Ru](Cl)Cl)=CC=1>[CH3:17][CH:14]1[CH:15]=[CH:16][C:3]2[C:12](=[CH:11][CH:10]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:4]=2)[O:13]1

Participants

4

Reactant 1

HCID 22313426HCID 22313426, compound

Product 1

HCID 22313331HCID 22313331, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 11967259Benzylidenebis(tricyclohexylphosphine)dichlororutheniumCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 3-formyl-4-[(1-methylprop-2-enyl)oxy]benzoate (370 mg, 1.59 mmol) in CH2Cl2 (8 mL) at rt is added benzylidene-bis(tricyclohexylphosphine)dichlororuthenium (56 mg, 0.068 mmol). The mixture is stirred at rt overnight. 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 225 mg (69%) of methyl 2-methyl-2H-chromene-6-carboxylate as a clear oil: 1H NMR (400 MHz, CDCl3) δ 7.82, 7.68, 6.79, 6.41, 5.71, 5.11, 3.89, 1.48.

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-f328e8f8cab94066807388245b59ce17
Source dataset
uspto-grants-2005_10
Patent number
US06951868B2

Reaction notes

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