Boron trifluoride → HCID 178472760, compound

HRID 1093912Notes

Reaction equation

HRID 1093912 reaction equation
C[Si](C)(C)N[Si](C)(C)C.C([Li])CCC.C[N:16]1[CH:20]=[C:19]([C:21]([NH:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:22])[C:18]([C:30]([F:33])([F:32])[F:31])=[N:17]1.[C:34]1(=[O:38])[CH2:37][CH2:36][CH2:35]1.B(F)(F)F.[NH4+].[Cl-]>C1COCC1.CCCCCC>[CH2:28]([O:27][C:25](=[O:26])[CH:24]([C:34]1([OH:38])[CH2:37][CH2:36][CH2:35]1)[NH:23][C:21]([C:19]1[C:18]([C:30]([F:33])([F:32])[F:31])=[N:17][NH:16][CH:20]=1)=[O:22])[CH3:29]

Participants

9

Reactant 6

HCID 6356Boron trifluorideHCID 13838HexamethyldisilazaneHCID 14496CyclobutanoneHCID 25517Ammonium ChlorideHCID 57519475HCID 57519475, compoundHCID 178418339Butyllithium

Product 1

HCID 178472760HCID 178472760, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

23.0 ml of hexamethyldisilazane (mmol) were dissolved in 200 ml of THF, and 46 ml of 2.5M (115 mmol) of butyllithium solution in hexane were added dropwise at −78° C. After 30 min, 7.90 g (22.3 mmol) of ethyl [(1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbonyl)amino]acetate, dissolved in 50 ml of THF, were added dropwise, and the mixture was stirred at −78° C. for 1.5 h. 3.0 g (42.8 mmol) of cyclobutanone and 4.14 g (29.2 mmol) of BF3-etherate, dissolved in 50 ml of THF, were added dropwise, and the mixture was stirred at −78° C. for 2 h, at −50° C. for 1 h and at 0° C. for 1 h. 100 ml of saturated NH4Cl solution were added dropwise, and the mixture was stirred for 30 min. The organic phase was separated off and the solvents were removed under reduced pressure. This gave 9.88 g (100%) of colorless crystals which were reacted without further purification.

Workup

  1. additionwere added dropwise
  2. additionwere added dropwise
  3. stirringthe mixture was stirred at −78° C. for 2 h, at −50° C. for 1 h and at 0° C. for 1 h
  4. stirringthe mixture was stirred for 30 min
  5. customThe organic phase was separated off
  6. customthe solvents were removed under reduced pressure
  7. customThis gave 9.88 g (100%) of colorless crystals which were reacted without further purification

Sources & evidence

ORD record
ord-977435a933a54c47a38e2b89ecb55124
Source dataset
uspto-grants-2012_03
Patent number
US08133851B2

Reaction notes

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