Methanol → HCID 68285453, compound

HRID 1618893Notes

Reaction equation

HRID 1618893 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18](=[O:20])[CH3:19])[CH:2]=1.[CH:21](OC)(OC)[O:22]C.[CH3:28]O>[Br-].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:28][O:20][C:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[O:11][C:3]1[CH:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)([O:22][CH3:21])[CH3:19]

Participants

5

Reactant 3

HCID 887MethanolHCID 9005Trimethyl orthoformateHCID 68285598HCID 68285598, compound

Product 1

HCID 68285453HCID 68285453, compound

Reagents, catalysts & solvents 1

HCID 23500184Tetra-n-butylammonium tribromideCatalyst

Procedure

After 0.13 g of 1-[2-(quinolin-3-yloxy)-phenyl]-ethanone and 0.06 g of trimethyl orthoformate were dissolved in 1.5 ml of methanol, 0.02 g of tetrabutylammonium tribromide was added and the mixture was stirred for 4 days at room temperature. The reaction mixture was concentrated and then purified by silica gel column chromatography to obtain 0.08 g of 3-[2-(1,1-dimethoxy-ethyl)-phenoxy]-quinoline (Compound Number 27).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-a303b2d5563249d2a533a7b0dd331b38
Source dataset
uspto-grants-2014_07
Patent number
US08772200B2

Reaction notes

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