3,4-dihydro-2H-pyran → HCID 21714364, compound

HRID 1600619Notes

Reaction equation

HRID 1600619 reaction equation
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17])[CH2:3][CH2:4][OH:5].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:31]1[CH:36]=[CH:35][CH2:34][CH2:33][CH2:32]1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17])[CH2:3][CH2:4][O:5][CH:32]1[CH2:33][CH2:34][CH2:35][CH2:36][O:31]1

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 27795662-{Methyl[2-nitro-4-(trifluoromethyl)phenyl]amino}ethan-1-ol

Product 1

HCID 21714364HCID 21714364, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[N-methyl-N-(2-hydroxyethyl)-amino]-3-nitrobenzotrifluoride (29.0 g, 110 mmol), p-toluenesulfonic acid monohydrate (2.09 g, 11.0 mmol), 3,4-dihydro-2H-pyran (18.5 g, 220 mmol) and tetrahydrofuran (600 ml) was stirred at room temperature for 4.5 hours. Sodium hydrogencarbonate (10 g) was added to the reaction mixture and the resulting mixture was stirred at room temperature for 30 minutes, after which the insoluble materials were filtered off. The filtrate was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=5/95) to obtain an oil of 4-[N-methyl-N-[2-(2-tetrahydro-2H-pyranyl)oxyethyl]amino]-3-nitrobenzotrifluoride.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  2. filtrationafter which the insoluble materials were filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=5/95)

Sources & evidence

ORD record
ord-c0859f7904e84d4eb7672a47c1fe02c6
Source dataset
uspto-grants-1999_11
Patent number
US05977100

Reaction notes

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