Phenylacetic Acid → HCID 19969600, compound

HRID 974821Notes

Reaction equation

HRID 974821 reaction equation
C([Li])CCC.[C:6]1([CH2:12][C:13]([OH:15])=[O:14])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[CH2:17][CH2:18][CH2:19][CH:20]1[O:24][CH2:23][CH2:22][O:21]1.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31]Cl>C1COCC1.CCCCCC.CN(C)P(N(C)C)(N(C)C)=O>[C:6]1([C:12]([CH2:17][CH2:18][CH2:19][CH:20]2[O:24][CH2:23][CH2:22][O:21]2)([CH2:31][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][N:25]=2)[C:13]([OH:15])=[O:14])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 999Phenylacetic AcidHCID 23393Picolyl chlorideHCID 5520722-(3-Chloropropyl)-1,3-dioxolaneHCID 178418339Butyllithium2×

Product 1

HCID 19969600HCID 19969600, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

A 2.5M hexane solution of butyl lithium (180 ml) was added to an ice-cooled solution of phenylacetic acid (20 g), hexamethylphosphoramide (25.6 ml) and tetrahydrofuran (260 ml). The reaction mixture was stirred to room temperature, then cooled back to 0° C. A solution of 2-(3-chloropropyl)-1,3-dioxolane in THF (20 ml) was added dropwise and the mixture was stirred to room temperature overnight. The reaction was cooled back down to 0° C. then butyl lithium (60 ml of a 2.5M hexane solution) was added dropwise followed by picolyl chloride (0.147 mol) in THF (40 ml). The ice-bath was removed and the reaction was stirred at room temperature for 3 days. The reaction mixture was quenched with half-saturated aqueous NH4Cl. Ethyl acetate and chloroform were added to dissolve the solids. The aqueous layer was neutralized with 1N HCl and extracted with chloroform. The combined organic layers were dried (MgSO4) and concentrated to give a solid which was washed with ether to give the subtitle compound (28.1 g).

Workup

  1. temperaturecooled back to 0° C
  2. stirringthe mixture was stirred to room temperature overnight
  3. temperatureThe reaction was cooled back down to 0° C.
  4. customThe ice-bath was removed
  5. stirringthe reaction was stirred at room temperature for 3 days
  6. customThe reaction mixture was quenched with half-saturated aqueous NH4Cl
  7. additionEthyl acetate and chloroform were added
  8. dissolutionto dissolve the solids
  9. extractionextracted with chloroform
  10. dry with materialThe combined organic layers were dried (MgSO4)
  11. concentrationconcentrated
  12. customto give a solid which
  13. washwas washed with ether

Sources & evidence

ORD record
ord-79b4224101e74e0b809ce385988867f1
Source dataset
uspto-grants-1997_03
Patent number
US05607935

Reaction notes

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