Diethyl Ether → 3-(4-{[1-(4-Chlorophenyl)-3-(trifluoromethyl)-1H-pyrrol-2-yl]methoxy}-2,3-dimethylphenyl)propan-1-ol
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[C:9]2[CH2:17][O:18][C:19]2[C:24](F)=[CH:23][C:22]([CH2:26][CH2:27][C:28](OCC)=[O:29])=[CH:21][C:20]=2F)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:40]([CH:43](C(C([O-])=O)O)O)([O-])=O.[K+].[Na+].C(OCC)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([F:14])([F:16])[F:15])=[C:9]2[CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:26][CH2:27][CH2:28][OH:29])=[C:21]([CH3:20])[C:40]=2[CH3:43])=[CH:6][CH:7]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of the product prepared in Example 1, Step E (46 mg, 0.10 mmol, 1 eq) in THF (2 mL) at 0° C. under N2 was added LAH (0.20 mL of a 1 M solution in THF, 0.20 mmol, 2 eq). After 1 hr, saturated sodium potassium tartrate (0.5 mL) was added dropwise at first, the solution was warmed to room temperature, diethyl ether was added, washed with brine, dried over MgSO4 and concentrated. The resulting residue was purified by flash chromatography (4 g column) eluting with 10 to 30% EtOAc/heptane to yield 3-(4-{[1-(4-Chlorophenyl)-3-(trifluoromethyl)-1H-pyrrol-2-yl]methoxy}-2,3-dimethylphenyl)propan-1-ol.
Workup
- washwashed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated
- customThe resulting residue was purified by flash chromatography (4 g column)
- washeluting with 10 to 30% EtOAc/heptane
Sources & evidence
- ORD record
- ord-90a6074ecfab4b8ba81e26214186c5ca
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045454B2
Reaction notes
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