Triphenylmethane → (S)-4-benzyl-3-(3,4-dichlorophenyl)acetyl-2-oxazolidinone

HRID 429467Notes

Reaction equation

HRID 429467 reaction equation
C1[N:6](CC2C=CC=CC=2)[C:4](=[O:5])[O:3]C1.C1([CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=CC=CC=2)C=CC=CC=1.C([Li])CCC.CC(C)(C)C(O[C:43](=[O:53])[CH2:44][C:45]1[CH:50]=[CH:49][C:48]([Cl:51])=[C:47]([Cl:52])[CH:46]=1)=O.[Li][C@H]1COC(=O)N1CC1C=CC=CC=1>C(OCC)(=O)C.CCCCCC.O1CCCC1>[CH2:20]([C@H:21]1[CH2:26][O:5][C:4](=[O:3])[N:6]1[C:43](=[O:53])[CH2:44][C:45]1[CH:50]=[CH:49][C:48]([Cl:51])=[C:47]([Cl:52])[CH:46]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

8

Reactant 5

HCID 10614TriphenylmethaneHCID 104875283-Benzyl-1,3-oxazolidin-2-oneHCID 539526903,4-Dichlorophenylacetic acid trimethylacetyl esterHCID 178418339ButyllithiumHCID 178506844HCID 178506844, compound

Product 1

HCID 69777551(S)-4-benzyl-3-(3,4-dichlorophenyl)acetyl-2-oxazolidinone

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent2×

Conditions

Temperature
-40 °C

Procedure

Alternately, combine (S)-benzyl-2-oxazolidinone (25 g, 140 mmol) and tetrahydrofuran (250 ml). Add triphenylmethane (30 mg) as an indicator. Cool to about −40° C. Add n-butyl lithium (about 56 ml, 1 M in hexane, 140 mmol) until an orange color persists. After 30 minutes, cool in a dry-ice/acetone bath the a solution of 3,4-dichlorophenylacetic acid trimethylacetyl ester as obtained in Preparation 3 and add by cannula the solution of lithio (S)-benzyl-2-oxazolidinone obtained above. When the addition is complete warm to ambient temperature. After 18 hours, partition the reaction mixture between diethyl ether and a saturated aqueous sodium bicarbonate solution. Separate the layers and dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially is with 5% ethyl acetate/hexane and 10% ethyl acetate/hexane to give (S)-4-benzyl-3-(3,4-dichlorophenyl)acetyl-2-oxazolidinone.

Workup

  1. customas obtained in Preparation 3
  2. customobtained above
  3. additionWhen the addition
  4. temperatureis complete warm to ambient temperature
  5. waitAfter 18 hours
  6. custompartition the reaction mixture between diethyl ether
  7. customSeparate the layers
  8. dry with materialdry the organic layer over MgSO4
  9. filtrationfilter
  10. customevaporate in vacuo
  11. customto give a residue

Sources & evidence

ORD record
ord-7e7c19cafc2d46ac9a413a7261ea5a7d
Source dataset
uspto-grants-2001_11
Patent number
US06316445B1

Reaction notes

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