Diethyl chlorophosphate → HCID 86620244, compound

HRID 639953Notes

Reaction equation

HRID 639953 reaction equation
[CH2:1]([C:3]1[CH:18]=[CH:17][C:6]([CH2:7][C:8]2[CH:16]=[CH:15][C:11]3[S:12][CH:13]=[CH:14][C:10]=3[CH:9]=2)=[CH:5][CH:4]=1)[CH3:2].C([Li])CCC.CCCCCC.[P:30](Cl)([O:35][CH2:36][CH3:37])([O:32][CH2:33][CH3:34])=[O:31]>C1COCC1>[CH2:33]([O:32][P:30]([C:13]1[S:12][C:11]2[CH:15]=[CH:16][C:8]([CH2:7][C:6]3[CH:17]=[CH:18][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=3)=[CH:9][C:10]=2[CH:14]=1)(=[O:31])[O:35][CH2:36][CH3:37])[CH3:34]

Participants

5

Reactant 3

HCID 13139Diethyl chlorophosphateHCID 68423034HCID 68423034, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 86620244HCID 86620244, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(4-ethylbenzyl)benzo[b]thiophene (1.50 g) in THF (11.8 mL) was added 2.44 M n-butyllithium/n-hexane solution (2.9 mL) at −78° C., and the reaction mixture was stirred for 1 hr at same temperature. Diethyl chlorophosphate (0.9 mL) was added to the reaction mixture at −78° C., and the reaction mixture was stirred for 0.5 hr at −78° C. The reaction was quenched by the addition of saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1/2) to give the title compound (1.79 g) as a colorless oil.

Workup

  1. stirringthe reaction mixture was stirred for 0.5 hr at −78° C
  2. customThe reaction was quenched by the addition of saturated aqueous ammonium chloride
  3. extractionextracted with ethyl acetate
  4. washThe combined ethyl acetate extracts were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1/2)

Sources & evidence

ORD record
ord-78a2b2add0c345148beea37d1485f795
Source dataset
uspto-grants-2010_04
Patent number
US07691898B2

Reaction notes

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