Boron trifluoride etherate → HCID 21072805, compound

HRID 1372922Notes

Reaction equation

HRID 1372922 reaction equation
[CH3:1][C:2]1([CH3:17])[O:7][C:6](=[O:8])[N:5]([CH2:9][CH2:10][C:11]#[N:12])[C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2.[CH2:18]([Mg]Br)[CH3:19].B(F)(F)F.CCOCC.[OH-].[Na+]>C(OCC)C.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[NH2:12][C:11]1([CH2:10][CH2:9][N:5]2[C:4]3[CH:13]=[CH:14][CH:15]=[CH:16][C:3]=3[C:2]([CH3:17])([CH3:1])[O:7][C:6]2=[O:8])[CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 21072837HCID 21072837, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 21072805HCID 21072805, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 3283Diethyl EtherSolvent3×

Procedure

A suspension of 6.0 g (26 mmol) 3-(4,4-dimethyl-2-oxo-4H-benzo[d][1,3]oxazin-1-yl]-propionitrile in 120 mL diethyl ether is combined with 16.5 mL (56 mmol) titanium tetra-isopropoxide while being cooled with an ice bath. Then 18.5 mL of a 3 molar solution of ethylmagnesium bromide in diethyl ether are added dropwise such that the temperature does not climb past 20° C. The mixture is stirred for 30 minutes at ambient temperature and 7.0 mL (55 mmol) boron trifluoride-diethyl ether are added batchwise while cooling with an ice bath. The mixture is stirred for one hour at ambient temperature and 150 mL 1 molar sodium hydroxide solution are added dropwise while cooling. The reaction mixture is diluted with diethyl ether and the phases are separated. The aqueous phase is extracted with diethyl ether and the combined organic phases are extracted with sodium sulphite solution and repeatedly extracted with 1 molar hydrochloric acid. The hydrochloric acid phases are combined, extracted with diethyl ether, made alkaline with sodium hydroxide solution and exhaustively extracted with dichloromethane. The dichloromethane phases are dried with sodium sulphate and evaporated down. Light yellow oil.

Workup

  1. temperaturewhile being cooled with an ice bath
  2. customdoes not climb past 20° C
  3. temperaturewhile cooling with an ice bath
  4. stirringThe mixture is stirred for one hour at ambient temperature
  5. temperaturewhile cooling
  6. customthe phases are separated
  7. extractionThe aqueous phase is extracted with diethyl ether
  8. extractionthe combined organic phases are extracted with sodium sulphite solution
  9. extractionrepeatedly extracted with 1 molar hydrochloric acid
  10. extractionextracted with diethyl ether
  11. extractionexhaustively extracted with dichloromethane
  12. dry with materialThe dichloromethane phases are dried with sodium sulphate
  13. customevaporated down

Sources & evidence

ORD record
ord-4b3e771777eb434ba61df9c40bdcd44a
Source dataset
uspto-grants-2007_01
Patent number
US07160882B2

Reaction notes

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