3,4-dihydro-2H-pyran → HCID 20081831, compound

HRID 1609562Notes

Reaction equation

HRID 1609562 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[CH:24]([C:27]1[C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:31]([C:38]2[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=2)[C:30]([CH2:45][OH:46])=[C:29]([CH:47]([CH3:49])[CH3:48])[N:28]=1)([CH3:26])[CH3:25]>ClCCl>[CH:24]([C:27]1[C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:31]([C:38]2[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=2)[C:30]([CH2:45][O:46][CH:6]2[CH2:5][CH2:4][CH2:3][CH2:2][O:1]2)=[C:29]([CH:47]([CH3:48])[CH3:49])[N:28]=1)([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10291957Ethyl 2,6-Diisopropyl-4-(4-fluorophenyl)-3-hydroxymethylpyridine-5-carboxylate

Product 1

HCID 20081831HCID 20081831, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.88 g (22.4 mmol) of dihydropyran and 0.525 g (1.49 mmol) of pyridinium p-toluene-sulphonate are added to a solution of 5.36 g (14.9 mmol) of the compound from Example 4 in 100 ml of dry dichloromethane and the mixture is heated to reflux for 48 hours. After cooling to room temperature, the mixture is diluted using dichloromethane and extracted several times using water. The organic phase is dried over magnesium sulphate and concentrated in vacuo, and the residue is chromatographed on a column (silica gel 70-230 mesh, using dichloromethane).

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 48 hours
  3. additionthe mixture is diluted
  4. extractionextracted several times
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customthe residue is chromatographed on a column (silica gel 70-230 mesh, using dichloromethane)

Sources & evidence

ORD record
ord-50af4557216345339a3ad2657da13c0a
Source dataset
uspto-grants-1995_03
Patent number
US05401746

Reaction notes

Loading…