HCID 22313292, compound → ethyl 2H-chromene-6-carboxylate

HRID 965843Notes

Reaction equation

HRID 965843 reaction equation
[CH2:1]([O:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][C:6]=1[CH:16]=[CH2:17])C=C>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:6](=[CH:7][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:14][CH:15]=2)[CH:16]=[CH:17][CH2:1]1

Participants

3

Reactant 1

HCID 22313292HCID 22313292, compound

Product 1

HCID 22313317ethyl 2H-chromene-6-carboxylateYield 82.7%

Reagents, catalysts & solvents 1

HCID 11967259Benzylidenebis(tricyclohexylphosphine)dichlororutheniumCatalyst

Procedure

To a stirred solution of ethyl 4-(allyloxy)-3-vinylbenzoate (1.8 g, 7.7 mmol) in CH2Ci2 (40 mL) at rt is added benzylidene-bis(tricyclohexylphosphine)dichlororuthenium (127 mg, 0.15 mmol). The mixture is stirred at rt for 2.5 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 1.3 g (80%) of ethyl 2H-chromene-6-carboxylate as a clear oil: 1H NMR (400 MHz, CDCl3) δ 7.8, 7.7, 6.8, 6.4, 5.8, 4.9, 4.4, 1.4.

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-a52c09c69253472baa09db874f907021
Source dataset
uspto-grants-2005_10
Patent number
US06951868B2

Reaction notes

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