Toluene → HCID 13914279, compound

HRID 2352348Notes

Reaction equation

HRID 2352348 reaction equation
[CH2:1]([N:3]([CH2:6]C)CC)C.[O:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.[CH2:13](Br)[C:14]#[CH:15].[C:17]1([CH3:23])C=CC=C[CH:18]=1.C(OCC)(=[O:26])C>O>[OH:8][C:12]1[CH:11]=[C:10]([C@H:9]([CH2:1][N:3]([CH3:6])[CH2:23][C:17]#[CH:18])[OH:26])[CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 7842Propargyl bromideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 8857Ethyl Acetate

Product 1

HCID 13914279HCID 13914279, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 20 g (0.098 mol) of R(-)phenylephrine hydrochloride, 20 g (0.2 mol) triethylamine and 300 ml of tetrahydrofuran is added a mixture of 12 g (0.1 mol) of propargyl bromide and 3 g of toluene over a period of 1/2 hour. The mixture is stirred for 16 hours and poured into water and ethyl acetate. The ethyl acetate is separated and the aqueous phase is extracted twice with ethyl acetate. The combined ethyl acetate is washed twice with dilute aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated to obtain crystals (14 g) m.p. 102°-103° C. The crystals are dissolved in hot ethyl acetate and the solution is diluted with hexane to obtain crystals (8.8 g) m.p. 102°-103° C.

Workup

  1. additionis added
  2. customThe ethyl acetate is separated
  3. extractionthe aqueous phase is extracted twice with ethyl acetate
  4. washThe combined ethyl acetate is washed twice with dilute aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d5f98e6879014c63b5b1ba7060dcfd2f
Source dataset
uspto-grants-1989_10
Patent number
US04876346

Reaction notes

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