Hydrochloric Acid → HCID 54395392, compound

HRID 1060582Notes

Reaction equation

HRID 1060582 reaction equation
C(N(CC)CC)C.[Br-].[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH:16]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[O:15][C:14]2=[O:39].[Cl:40][C:41]1[CH:42]=[N:43][CH:44]=[C:45]([Cl:49])[C:46]=1[CH:47]=O.Cl>C(Cl)Cl>[Cl:40][C:41]1[CH:42]=[N:43][CH:44]=[C:45]([Cl:49])[C:46]=1[CH:47]=[C:16]1[C:17]2[C:13](=[CH:12][C:11]([O:10][CH3:9])=[CH:19][CH:18]=2)[C:14](=[O:39])[O:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27629883,5-Dichloro-4-pyridinecarboxaldehydeHCID 11562468(5-Methoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)triphenyl phosphonium bromide

Product 1

HCID 54395392HCID 54395392, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (18.5 ml, 0.134 moles) was dropwise added to a suspension of (5-methoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)triphenyl phosphonium bromide (74 g. 0.134 moles) obtained as described in example 10, and 3,5-dichloro-pyridin-4-carbaldehyde (23.6 g, 0.134 moles) in CH2Cl2 (500 ml) under N2 by controlling the temperature with a water-bath. The mixture was kept under stirring overnight, then cooled and treated with 5% HCl. The phases were separated and the acid one was re-extracted with CH2Cl2, washed with water/NaCl, decoloured with charcoal, dried and concentrated under high vacuum. There were obtained 85.4 g of a crude which was used as such in the subsequent step. A sample of the crude was purified by flash chromatography (eluent:hexane/ethyl acetate 1:1).

Workup

  1. customobtained
  2. temperaturecooled
  3. customThe phases were separated
  4. extractionthe acid one was re-extracted with CH2Cl2
  5. washwashed with water/NaCl
  6. customdried
  7. concentrationconcentrated under high vacuum
  8. customThere were obtained 85.4 g of a crude which
  9. customA sample of the crude was purified by flash chromatography (eluent:hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-7d7f1dd7945c4be6ac083137c0199999
Source dataset
uspto-grants-2003_02
Patent number
US06525055B1

Reaction notes

Loading…