3,4-dihydro-2H-pyran → HCID 11011298, compound

HRID 2242037Notes

Reaction equation

HRID 2242037 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:6][CH:7]=1.[O:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[CH3:12][C:10]([CH3:11])([CH3:13])[C:9]([NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:1][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][O:15]2)[CH:3]=1)=[O:14]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 4186956HCID 4186956, compound

Product 1

HCID 11011298HCID 11011298, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

N-(3-Hydroxy-phenyl)-2,2-dimethyl-propionamide (49 g, 0.254 mol) in dichloromethane (1 l) is treated with dihydropyrane (66 ml, 0.762 mol) and pyridinium p-toluenesulfonate (957 mg, 3.8 mmol). After stirring for 6 days at 25° C., the solvent is removed and the residue crystallized from EtOAc/hexanes to give 2,2-dimethyl-N-[3-(tetrahydro-pyran-2-yloxy)-phenyl]-propionamide.

Workup

  1. customthe solvent is removed
  2. customthe residue crystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-492cdfd7581449cd927ab9a3366558cb
Source dataset
uspto-grants-2010_03
Patent number
US07671063B2

Reaction notes

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