Chlorotrimethylsilane → HCID 86747713, compound

HRID 488070Notes

Reaction equation

HRID 488070 reaction equation
[Cl:1][CH2:2][C:3](=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].[CH3:10][Si:11](Cl)([CH3:13])[CH3:12].C(N(CC)CC)C>C(OCC)(=O)C>[Cl:1][CH2:2]/[C:3](/[O:9][Si:11]([CH3:13])([CH3:12])[CH3:10])=[CH:4]/[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 36240Methyl 4-chloroacetoacetate

Product 1

HCID 86747713HCID 86747713, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-chloro-3-oxobutanoic acid, methyl ester (60.4 g, 0.4 mol) and trimethylsilyl chloride (48.8 mL, 1.3 mol) in 500 mL dry ethyl acetate was cooled to -20° C. and triethylamine (17.42 mL, 1.25 mol) was added dropwise over 15 minutes under nitrogen atmosphere. The cold bath was removed and the heterogeneous mixture was stirred for two hours. The mixture was diluted with 200 mL dry hexane, stirred for five minutes and filtered under nitrogen. The filtrate was evaporated under vaccum. The product was redissolved in 100 mL hexane and filtered to remove a small amount of TEA.HCl. The filtrate was evaporated and the product was kept under pump vaccum for 0.5 hours to give the title compound (83.95 g, 94%).

Workup

  1. customThe cold bath was removed
  2. additionThe mixture was diluted with 200 mL dry hexane
  3. stirringstirred for five minutes
  4. filtrationfiltered under nitrogen
  5. customThe filtrate was evaporated under vaccum
  6. dissolutionThe product was redissolved in 100 mL hexane
  7. filtrationfiltered
  8. customto remove a small amount of TEA
  9. customThe filtrate was evaporated
  10. waitthe product was kept under pump vaccum for 0.5 hours

Sources & evidence

ORD record
ord-863444b5cee24b768b70fa1146ebb3fc
Source dataset
uspto-grants-1994_03
Patent number
US05298625

Reaction notes

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