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

HRID 2061432Notes

Reaction equation

HRID 2061432 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

To a solution of 3-amino-phenol (60 g, 6.55 mol) in 2 N NaOH (1 l), cooled to 10° C., pivaloyl chloride (68 ml, 0.55 mol) in toluene (200 ml) is added within 1 h. After stirring for 15 h at 25° C., the mixture is cooled to 0° C. and acidified to pH 1 with conc. HCl. Extraction with EtOAc washing with water, 10% NaHCO3, water, and brine, followed by drying (Na2SO4), evaporation of volatiles, and crystallization (EtOAc/hexanes) gives N-(3-hydroxy-phenyl)-2,2-dimethyl-propionamide. 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-6ff5b54023b945b490e87f2279c425a8
Source dataset
uspto-grants-2012_10
Patent number
US08283356B2

Reaction notes

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