3,4-dihydro-2H-pyran → HCID 66607810, compound

HRID 717122Notes

Reaction equation

HRID 717122 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][CH:11]=[N:10][N:9]=2)=[CH:4][C:3]=1[CH3:13].[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1>O1CCCC1.C(OCC)(=O)C.CS(O)(=O)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19][O:14]3)[CH:11]=[N:10][N:9]=2)=[CH:4][C:3]=1[CH3:13]

Participants

6

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 178423521HCID 178423521, compound

Product 1

HCID 66607810HCID 66607810, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 6395Methanesulfonic AcidCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
50 °C

Procedure

3-(4-Bromo-3-methylphenyl)-4H-1,2,4-triazole (2.00 g, 8.40 mmol) was dissolved in tetrahydrofuran (10 mL) at room temperature with stirring under nitrogen. 3,4-Dihydro-2H-pyran (3.80 mL, 42.0 mmol) and methanesulfonic acid (0.027 mL, 0.42 mmol) were added and the resulting mixture heated at 50° C. under a reflux condenser under nitrogen for 20 h. The resulting mixture was cooled to room temperature, diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate and brine. The organics were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Flash chromatography (10-30-50% ethyl acetate in hexanes) gave the desired product (2.64 g, 8.22 mmol, 98% yield) as a yellow oil. MS (ESI) m/z 322 [M]+, 324 [M+2]+.

Workup

  1. temperatureThe resulting mixture was cooled to room temperature
  2. washwashed with saturated aqueous sodium bicarbonate and brine
  3. dry with materialThe organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-58d3d4f400de48e396e4fb8d09862c93
Source dataset
uspto-grants-2015_11
Patent number
US09193692B2

Reaction notes

Loading…