Diethyl Ether → HCID 86718611, compound
Reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:17]2[CH:18]=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=2)[C:8]([O:13][CH2:14][O:15][CH3:16])=[C:9]([CH:12]=1)[CH:10]=[O:11])([CH3:4])([CH3:3])[CH3:2].[CH3:27][Mg]Br.C(OCC)C>C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]([C:17]2[CH:18]=[N:19][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:21][CH:22]=2)[C:8]([O:13][CH2:14][O:15][CH3:16])=[C:9]([CH:10]([OH:11])[CH3:27])[CH:12]=1)([CH3:4])([CH3:2])[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 5-(tert-butyl)-2-(methoxymethoxy)-3-(6-(trifluoromethyl)pyridin-3-yl)benzaldehyde (1.0 g, 2.72 mmol) in THF (15 mL) at −78° C. under argon was added a 3 M solution of methyl magnesium bromide in diethyl ether (1.0 mL, 3.0 mmol). The reaction mixture was stirred at −78° C. for 10 minutes and then the solution poured onto brine cooled to 0° C. forming a gel. The mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution. The organic phase was separated, dried (Na2SO4), filtered, and the solvent removed under reduced pressure to give 1-(5-(tert-butyl)-2-(methoxymethoxy)-3-(6-(trifluoromethyl)pyridin-3-yl)phenyl)ethan-1-ol (660 mg, 63% yield) as a tan oil.
Workup
- additionthe solution poured onto brine
- temperaturecooled to 0° C.
- customforming a gel
- customThe mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution
- customThe organic phase was separated
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customthe solvent removed under reduced pressure
Sources & evidence
- ORD record
- ord-fc9daea1648d42beb29ffe92ed80c350
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409893B2
Reaction notes
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