Allyltrimethylsilane → HCID 21706235, compound

HRID 1594924Notes

Reaction equation

HRID 1594924 reaction equation
O[C:2]1([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)[O:7][CH2:6][CH2:5][N:4]([CH3:8])[C:3]1=[O:9].[CH2:18]([Si](C)(C)C)[CH:19]=[CH2:20]>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH2:20]([C:2]1([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)[O:7][CH2:6][CH2:5][N:4]([CH3:8])[C:3]1=[O:9])[CH:19]=[CH2:18]

Participants

5

Reactant 2

HCID 69808AllyltrimethylsilaneHCID 21706241HCID 21706241, compound

Product 1

HCID 21706235HCID 21706235, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
-23 °C

Procedure

Following the procedure described by S. Pansare et al., J. Org. Chem. 1998, 63, 4120-4124, 2-hydroxy-2-(3-methoxy-phenyl)-4-methyl-morpholin-3-one, as described in Step C above, (0.133 g, 0.56 mmol) was dissolved in anhydrous CH2Cl2 (10 mL) under Ar, treated with allyltrimethylsilane (0.534 mL, 3.36 mmol), the mixture cooled to −23° C., then treated with TiCl4 (0.37 mL, 3.36 mmol). After 15 min the reaction mixture was quenched slowly with saturated aqueous NH4Cl solution, left to warm to room temperature, and partitioned between CH2Cl2 and H2O. The aqueous layer was washed with CH2Cl2, the organic layers combined, dried (Na2SO4), filtered and concentrated to dryness to give the title compound after chromatography (SiO2, 0-1% MeOH in CH2Cl2).

Workup

  1. customAfter 15 min the reaction mixture was quenched slowly with saturated aqueous NH4Cl solution
  2. waitleft
  3. temperatureto warm to room temperature
  4. custompartitioned between CH2Cl2 and H2O
  5. washThe aqueous layer was washed with CH2Cl2
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e90635e6eb4a4881877b20a5717bb7b1
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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