HCID 89705088, compound → HCID 89704989, compound

HRID 59673Notes

Reaction equation

HRID 59673 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]#[CH:17])[C:5]=1[C:6]([O:8][CH3:9])=[O:7]>C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][C:4]1[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:10]2[C:11]([CH:17]=[CH:16][CH2:15][O:14]2)=[CH:12][CH:13]=1

Participants

3

Reactant 1

HCID 89705088HCID 89705088, compound2×

Product 1

HCID 89704989HCID 89704989, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of methyl 2-methoxymethyl-6-propargyloxybenzoate (Intermediate 10, 1.4 g) and [Bis-(trifluoromethanesulfonyl)imidate](triphenyl phosphine) gold 2:1 complex with toluene (0.188 g) in toluene (40 mL) was stirred and heated under an atmosphere of nitrogen overnight. After cooling, the mixture was filtered through Celite and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica, eluting with a mixture of TBME and cyclohexane with a gradient of 0-30% to give methyl 7-methoxymethyl-2H-chromene-8-carboxylate (0.875 g) as an oil.

Workup

  1. temperatureheated under an atmosphere of nitrogen overnight
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered through Celite
  4. customthe filtrate was evaporated to dryness
  5. customThe residue was purified by chromatography on silica
  6. washeluting with a mixture of TBME and cyclohexane with a gradient of 0-30%

Sources & evidence

ORD record
ord-2ef1d04fd0f94227afa4421e090ba1a4
Source dataset
uspto-grants-2016_09
Patent number
US09440943B2

Reaction notes

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