Lithium diisopropylamide → HCID 15031229, compound
Reaction equation
[F:1][CH:2]([F:11])[P:3]([O:8][CH2:9][CH3:10])(=[O:7])[O:4][CH2:5][CH3:6].C([N-]C(C)C)(C)C.[Li+].Br[C:21]1([CH3:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]1[CH3:27]>O1CCCC1>[CH3:28][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][C:2]([P:3](=[O:7])([O:8][CH2:9][CH3:10])[O:4][CH2:5][CH3:6])([F:1])[F:11]Participants
Conditions
- Temperature
- -78 °C
Procedure
30 mmol (5.64 g) of diethyl difluoromethane phosphonate dissolved in 30 ml of anhydrous tetrahydrofuran (THF) are slowly added to a stirred solution of (LDA) lithium diisopropylamide (prepared at 0° C. from 31 mmol of n-butyllithium and 30 mmol of diisopropylamine in 30 ml of anhydrous THF) at -78° C. under argon. After 30 minutes, 45 mmol (8.33 g) of 2-bromo-o-xylene are added to the reaction mixture which is stirred at -78° C. for 15 hours and quenched by adding 20 ml of an aqueous saturated solution of ammonium chloride. The crude mixture is evaporated to dryness; the residue is suspended in 50 ml of water and extracted 3 times with 100 ml of ethylacetate. The organic layers are dried over sodium sulfate, filtered and evaporated to give approximately 8 g of crude product which is purified by flash chromotography on silica gel affording 3.6 g of 1A (41% yield).
Workup
- customquenched
- additionby adding 20 ml of an aqueous saturated solution of ammonium chloride
- customThe crude mixture is evaporated to dryness
- extractionextracted 3 times with 100 ml of ethylacetate
- dry with materialThe organic layers are dried over sodium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-b43eeb05c5d8455894f48c02c2621e03
- Source dataset
- uspto-grants-1996_02
- Patent number
- US05494912
Reaction notes
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