Lithium diisopropylamide → 4-Trimethylsilyloxy-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-octyl-2-cyclopentenone
Reaction equation
[CH3:1][Si:2]([CH3:19])([CH3:18])[O:3][C@:4]1([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:8][C:7](=[O:9])[CH:6]=[CH:5]1.[Li+].CC([N-]C(C)C)C.C([NH-])(C)C.C([Li])CCC.[CH:37]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]([O:46][CH3:47])=[O:45])=[O:38]>O1CCCC1.CCCCCC>[CH3:1][Si:2]([CH3:18])([CH3:19])[O:3][C:4]1([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:8]([CH:37]([OH:38])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]([O:46][CH3:47])=[O:45])[C:7](=[O:9])[CH:6]=[CH:5]1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
Under a nitrogen atmosphere at -78° C., a solution of 200 mg (0.71 mmole) of (4R)-4-trimethylsilyloxy-4-octyl-2-cyclopentenone in 2 ml of tetrahydrofuran was added to a solution of LDA prepared from 93 mg (0.92 mmole) of isopropylamide and 590 microliters of n-butyllithium (as a 10 W/V % hexane solution) in 3 ml of tetrahydrofuran, and the mixture was stirred for 1 hour. Then, a solution of 146 mg (0.92 mmole) of methyl 6-formylhexanoate in 2 ml of tetrahydrofuran was added, and the mixture was stirred at -78° C. for 2 hours. The reaction was terminated by adding an aqueous solution of ammonium chloride. The reaction mixture was extracted with ether, and the extract was dried over anhydrous magnesium sulfate, filtered and concentrated.
Workup
- stirringthe mixture was stirred at -78° C. for 2 hours
- customThe reaction was terminated
- additionby adding an aqueous solution of ammonium chloride
- extractionThe reaction mixture was extracted with ether
- dry with materialthe extract was dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5289f19d942d4f9d850c5379261cf8ac
- Source dataset
- uspto-grants-1987_12
- Patent number
- US04711895
Reaction notes
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