Tetrahydrofuran → HCID 67276589, compound
Reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[K+].C1COCC1.[CH3:16][O:17][C:18]1[CH:35]=[CH:34][C:21]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30](=[O:33])[CH2:31][CH3:32])=[CH:26][CH:25]=2)=[CH:20][CH:19]=1.[C:36]([Si:40]([CH3:43])([CH3:42])Cl)([CH3:39])([CH3:38])[CH3:37]>O>[C:36]([Si:40]([O:33]/[C:30](/[C:27]1[CH:28]=[CH:29][C:24]([O:23][CH2:22][C:21]2[CH:34]=[CH:35][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)=[CH:25][CH:26]=1)=[CH:31]\[CH3:32])([CH3:43])[CH3:42])([CH3:39])([CH3:38])[CH3:37]Participants
6
Procedure
With cooling with ice, potassium hexamethyldisilazide (0.5 M toluene solution, 89 mL) was dropwise added to a stirring THF (100 mL) solution of the compound (10.0 g, 37.0 mmol) synthesized in the above (1) and t-butyldimethylchlorosilane (6.13 g, 40.7 mmol), and then the reaction solution was stirred at room temperature for 12 hours. The reaction solution was poured into water, extracted with ethyl acetate, the organic layer was washed with saturated saline, and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel flash column chromatography (hexane) to obtain the entitled compound (13.5 g, 95%) as a white solid.
Workup
- extractionextracted with ethyl acetate
- washthe organic layer was washed with saturated saline
- dry with materialdried with magnesium sulfate
- customThe solvent was removed under reduced pressure
- customthe residue was purified by silica gel flash column chromatography (hexane)
Sources & evidence
- ORD record
- ord-0e737b27ac404e93b7ed5bb52f53cbb7
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163770B2
Reaction notes
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