HCID 90460626, compound → HCID 90460678, compound

HRID 1846251Notes

Reaction equation

HRID 1846251 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:16]2[N:20]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][O:22]3)[N:19]=[C:18]([CH3:27])[C:17]=2[CH2:28][OH:29])[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1>ClCCl.O=[Mn]=O>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:16]2[N:20]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][O:22]3)[N:19]=[C:18]([CH3:27])[C:17]=2[CH:28]=[O:29])[CH:9]=[C:10]([C:12]([F:13])([F:15])[F:14])[CH:11]=1

Participants

4

Reactant 1

HCID 90460626HCID 90460626, compound

Product 1

HCID 90460678HCID 90460678, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of (R/S) (5-(3-(2-methoxyethoxy)-5-(trifluoromethyl)phenyl)-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methanol (320 mg, 0.77 mmol, 1.00 equiv) and MnO2 (672 mg, 7.73 mmol, 10.01 equiv) in dichloromethane (40 mL) was stirred at 40° C. for 3 h. The reaction mixture of cooled to room temperature and the solid material was removed by filtration. The filtrate was concentrated under vacuum to give 300 mg (94%) of (R/S) 5-(3-(2-methoxyethoxy)-5-(trifluoromethyl)phenyl)-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carbaldehyde as a yellow oil. LCMS (method D, ESI): RT=1.61 min, m/z=413.0 [M+H]+.

Workup

  1. additionThe reaction mixture
  2. temperatureof cooled to room temperature
  3. customthe solid material was removed by filtration
  4. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-f4da0b9f25844789b5494eb59bca3184
Source dataset
uspto-grants-2015_02
Patent number
US08952026B2

Reaction notes

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