3,4-dihydro-2H-pyran → HCID 21949789, compound

HRID 2215362Notes

Reaction equation

HRID 2215362 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8]([CH3:9])=[C:7]([OH:10])[C:6]([C:11]([F:14])([F:13])[F:12])=[N:5]1.[O:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1>ClCCl.C(OCC)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:9][C:8]1[N:4]([CH2:3][CH2:2][O:1][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][O:15]2)[N:5]=[C:6]([C:11]([F:14])([F:13])[F:12])[C:7]=1[OH:10]

Participants

6

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 21949875HCID 21949875, compound

Product 1

HCID 21949789HCID 21949789, compoundYield 66.5%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-(2-hydroxyethyl)-5-methyl-3-(trifluoromethyl)-1H-pyrazol-4-ol (600 mg, 2.86 mmol; Kenkyu Hokoku—Asahi Garasu Kogyo Gijutsu Shoreikai, 1988, 51, 139–49) in dichloromethane (10 ml) and ethyl acetate (4 ml) was added para-toluenesulphonic acid (27 mg, 0.14 mmol) followed by 3,4-dihydro-2H-pyran (340 μl, 3.7 mmol). The reaction mixture was stirred at room temperature for 3 hours before being concentrated under reduced pressure. The crude product mixture was purified by flash chromatography on silica gel eluting with pentane:ethyl acetate (60:40, by volume) to provide the title compound (560 mg) as white solid.

Workup

  1. concentrationbefore being concentrated under reduced pressure
  2. customThe crude product mixture was purified by flash chromatography on silica gel eluting with pentane:ethyl acetate (60:40, by volume)

Sources & evidence

ORD record
ord-81b8b9d96e7b42f484f58dabc78b066f
Source dataset
uspto-grants-2006_09
Patent number
US07109228B2

Reaction notes

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