Water → HCID 54342974, compound

HRID 2379014Notes

Reaction equation

HRID 2379014 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH2:10][C@H:11]([CH:13]([CH3:15])[CH3:14])[N:12]=2)=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[CH:23]=[O:24].O>O1CCCC1.CCCCCC>[CH:23]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH2:10][C@H:11]([CH:13]([CH3:15])[CH3:14])[N:12]=2)=[CH:4][CH:3]=1)=[O:24]

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 11514533HCID 11514533, compoundHCID 178418339Butyllithium

Product 1

HCID 54342974HCID 54342974, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 2 g of (S)-2-(4-bromophenyl)-4-isopropyl-2-oxazoline in 20 ml of absolute tetrahydrofuran is treated drop-wise with 5 ml of 1.6M butyllithium in hexane at -78° C. and while gassing with nitrogen, stirred at this temperature for 2 hours, then treated dropwise with 2 ml of absolute N,N-dimethyl-formamide and then warmed slowly to room temperature. The reaction mixture is poured into 100 ml of water and extracted three times with 50 ml of diethyl ether each time. The combined organic phases are washed twice with 100 ml of saturated sodium chloride solution each time, dried over magnesium sulphate, filtered and then concentrated. Chromatography of the residue on silica gel with hexane/ethyl acetate (vol. 9:1) yields 0.8 g of pure (S)-2-(4-formylphenyl)-4-isopropyl-2-oxazoline.

Workup

  1. extractionextracted three times with 50 ml of diethyl ether each time
  2. washThe combined organic phases are washed twice with 100 ml of saturated sodium chloride solution each time
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b1455f85e96c4925a91f300d5b71745f
Source dataset
uspto-grants-1994_11
Patent number
US05360577

Reaction notes

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