3,4-dihydro-2H-pyran → HCID 19429856, compound

HRID 1492040Notes

Reaction equation

HRID 1492040 reaction equation
CO[C:3](=[O:22])[C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=1)=[N:5][O:6][CH3:7].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+:37]=[CH:36]C=1.[O:40]1[CH:45]=[CH:44][CH2:43][CH2:42][CH2:41]1>ClCCl>[CH3:36][NH:37][C:3](=[O:22])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH:45]2[CH2:44][CH2:43][CH2:42][CH2:41][O:40]2)[CH:16]=1)=[N:5]/[O:6][CH3:7]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 53834306HCID 53834306, compound

Product 1

HCID 19429856HCID 19429856, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl-2-[2-(3-hydroxyphenoxy)phenyl]-2-methoxyiminoacetate (0.25 g) in dichloromethane (10 ml), dihydropyrane (0.3 ml) and PPTS (20 mg) were added, and the resultant mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with dichloromethane, washed with a saturated aqueous sodium hydrogencarbonate solution, followed by removal of the solvent. The residue was dissolved in methanol (3 ml), and 40% methanolic methylamine (0.5 ml) was added thereto. The resultant mixture was stirred at room temperature for 15 hours. The solvent and excess methylamine were removed, and the residue was purified by silica gel column chromatography to give 0.27 g of the objective compound.

Workup

  1. washwashed with a saturated aqueous sodium hydrogencarbonate solution
  2. customfollowed by removal of the solvent
  3. dissolutionThe residue was dissolved in methanol (3 ml)
  4. addition40% methanolic methylamine (0.5 ml) was added
  5. customThe solvent and excess methylamine were removed
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8447dff1a9334e918d1c86472c0ce8b8
Source dataset
uspto-grants-1994_12
Patent number
US05371223

Reaction notes

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