Boron trifluoride etherate → HCID 68544684, compound

HRID 1432088Notes

Reaction equation

HRID 1432088 reaction equation
[CH2:1]([Mg]Cl)[CH:2]=C.B(F)(F)F.[CH3:10]COCC.[C:15]([N:20]1[C@H:24]([CH:25]([CH3:27])[CH3:26])[C:23]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:22][C:21]1=[O:40])(=[O:19])/[CH:16]=[CH:17]/[CH3:18]>C1COCC1.[Cu]I>[CH:25]([C@@H:24]1[C:23]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:22][C:21](=[O:40])[N:20]1[C:15](=[O:19])[CH2:16][C@H:17]([CH3:10])[CH2:18][CH:1]=[CH2:2])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 68541676HCID 68541676, compoundHCID 178418473HCID 178418473, compound

Product 1

HCID 68544684HCID 68544684, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a stirred suspension of 22.35 g (117 mmol) CuI in 400 ml THF at −40° C. are added dropwise 70 ml (140 mmol) of a 2M THF solution of allylmagnesium chloride. After 1 h the mixture is cooled to −78° C. and 17.7 ml (140 mmol) BF3.OEt2 are added in 15 minutes. Then a solution of 41 g (117 mmol) (R)-3-((E)-but-2-enoyl)-4-isopropyl-5,5-diphenyl-oxazolidin-2-one in 100 ml THF is added as quickly as possible. The temperature rises to −40° C. Stirring is continued for 1 h and then the mixture is quenched with 500 ml 10% aqueous NH4Cl. The mixture is stirred for 1 h at 25° C. and filtered over celite and washed with 150 ml TBME. The organic phase is washed successively with water, 10% aqueous NaHCO3, water, 5% citric acid and water. Chromatography (silica gel, EE/hexane 1:10) of the crude product yields the (R)-4isopropyl-3-((R)-3-methyl-hex-5-enoyl)-5,5-diphenyl-oxazolidin-2-one.

Workup

  1. customrises to −40° C
  2. customthe mixture is quenched with 500 ml 10% aqueous NH4Cl
  3. stirringThe mixture is stirred for 1 h at 25° C.
  4. filtrationfiltered over celite
  5. washwashed with 150 ml TBME
  6. washThe organic phase is washed successively with water, 10% aqueous NaHCO3, water, 5% citric acid and water

Sources & evidence

ORD record
ord-2754ebbfdb9240ee91be88d8a3e71beb
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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