Water → HCID 9932885, compound

HRID 611769Notes

Reaction equation

HRID 611769 reaction equation
[CH2:1]([Li])[CH2:2]CC.[CH2:6]([O:8][P:9]([CH:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]1[C:24]([O-:26])=[O:25])([O:11][CH2:12][CH3:13])=[O:10])[CH3:7].Br[CH2:28][CH2:29][CH:30]1[O:34][CH2:33][CH2:32][O:31]1.O>CCCCCC.O1CCCC1>[CH2:6]([O:8][P:9]([O:11][CH2:12][CH3:13])([CH:14]1[CH:23]=[C:22]([CH2:28][CH2:29][CH:30]2[O:34][CH2:33][CH2:32][O:31]2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]1[C:24]([O:26][CH2:1][CH3:2])=[O:25])=[O:10])[CH3:7]

Participants

7

Reactant 4

HCID 962WaterHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 131721490HCID 131721490, compoundHCID 178418339Butyllithium

Product 1

HCID 9932885HCID 9932885, compoundYield 62.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

75 ml of a 1.6 M solution of n-butyllithium in hexane is added at -78° C., to a solution containing 33.933 g of ethyl 2-(diethoxyphosphinyl-1(2H)-quinoline carboxylate in 500 ml of tetrahydrofuran. Next 18 ml of 2-(2-bromoethyl)-1,3-dioxolane is added. The reaction medium is allowed to return to ambient temperature, then maintained under agitation for 5 hours. 300 ml of water is added, followed by agitation and decanting. The organic phase is washed with water and dried followed by filtration and elimination of the solvent. 63.45 g of product is obtained which is purified by chromatography eluting with ethyl acetate. In this way the sought product is obtained.

Workup

  1. customto return to ambient temperature
  2. temperaturemaintained under agitation for 5 hours
  3. customdecanting
  4. washThe organic phase is washed with water
  5. customdried
  6. filtrationfollowed by filtration and elimination of the solvent

Sources & evidence

ORD record
ord-5a9f27ed6b1d4c2c8b3f34bfc443775a
Source dataset
uspto-grants-1999_12
Patent number
US06002006

Reaction notes

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