Triethylamine → HCID 53744793, compound

HRID 2300048Notes

Reaction equation

HRID 2300048 reaction equation
C(N(CC)CC)C.[Br-].[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[CH:16]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[O:15][C:14]2=[O:41].[N:42]1[CH:47]=[CH:46][C:45]([CH:48]=O)=[CH:44][CH:43]=1>C(Cl)Cl>[CH3:21][O:20][C:19]1[CH:18]=[C:17]2[C:13](=[CH:12][C:11]=1[O:10][CH3:9])[C:14](=[O:41])[O:15][C:16]2=[CH:48][C:45]1[CH:46]=[CH:47][N:42]=[CH:43][CH:44]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 133894-PyridinecarboxaldehydeHCID 11466779(5,6-Dimethoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-triphenylphosphonium bromide

Product 1

HCID 53744793HCID 53744793, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (20 ml, 145 mmoles) was added dropwise to a suspension of (5,6-dimethoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-triphenylphosphonium bromide (78 g, 145 mmoles), obtained as described in example 12, and 4-pyridincarboxaldehyde (13.0 ml, 145 mmoles) in methylene chloride (1 l), at room temperature, under stirring. After 1.5 hours the mixture was filtered and evaporated and the residue was treated with boiling ethanol, cooled and filtered. The mother liquors were chromatographed (eluent: methylene chloride then with 1% methanol) and the residue was brought to dryness and joined to the above filtrate to give 25 g of the title compound.

Workup

  1. customobtained
  2. filtrationAfter 1.5 hours the mixture was filtered
  3. customevaporated
  4. additionthe residue was treated with boiling ethanol
  5. temperaturecooled
  6. filtrationfiltered
  7. customThe mother liquors were chromatographed (eluent

Sources & evidence

ORD record
ord-23225ce39f8d4dcd9c62056a477b5cc0
Source dataset
uspto-grants-2002_12
Patent number
US06498160B2

Reaction notes

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