Tetrahydrofuran → (2E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(((triisopropylsilyl)oxy)methylene)cyclohexanol
Reaction equation
O1CCCC1.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([Mg]Br)=[CH:9][CH:8]=1.[CH3:15][C:16]1([CH3:35])[CH2:21][CH2:20][C:19](=[O:22])/[C:18](=[CH:23]/[O:24][Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])/[CH2:17]1>C1(C)C=CC=CC=1>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:19]2([OH:22])[CH2:20][CH2:21][C:16]([CH3:15])([CH3:35])[CH2:17]/[C:18]/2=[CH:23]\[O:24][Si:25]([CH:26]([CH3:28])[CH3:27])([CH:32]([CH3:34])[CH3:33])[CH:29]([CH3:31])[CH3:30])=[CH:9][CH:8]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -2.5 °C
Procedure
To EXAMPLE 2 (26 g, as a solution in toluene) was added to anhydrous tetrahydrofuran (65 mL). The resulting mixture was cooled to −5 to 0° C. A separate flask was charged with anhydrous tetrahydrofuran (65 mL) and a 1 M solution of (4-chlorophenyl)magnesium bromide (172 mL, 2.05 equiv). The reagent mixture was cooled to −5 to 0° C. The mixture of EXAMPLE 2 in toluene was slowly added to the Grignard reagent, maintaining a reaction temperature below 5° C. The reaction was monitored by HPLC and was determined to be complete in about one hour. The reaction mixture was quenched slowly with methanol (91 mL), maintaining an internal temperature below 5° C.
Workup
- temperatureThe reagent mixture was cooled to −5 to 0° C
- temperaturemaintaining a reaction temperature below 5° C
- customThe reaction mixture was quenched slowly with methanol (91 mL)
- temperaturemaintaining an internal temperature below 5° C.
Sources & evidence
- ORD record
- ord-48f0e7b41112460a9c5746229d77a033
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08168784B2
Reaction notes
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