2-Bromo-1,1-dimethoxypropane → HCID 58191758, compound

HRID 1034611Notes

Reaction equation

HRID 1034611 reaction equation
CON(C)[C:4]([C:6]1[CH:11]=[C:10]([Br:12])[CH:9]=[CH:8][N:7]=1)=[O:5].[CH3:14][O:15][CH:16]([O:20][CH3:21])[CH:17](Br)[CH3:18]>C1COCC1.O.C(=O)=O>[Br:12][C:10]1[CH:9]=[CH:8][N:7]=[C:6]([C:4](=[O:5])[CH2:18][CH2:17][CH:16]([O:20][CH3:21])[O:15][CH3:14])[CH:11]=1

Participants

6

Reactant 2

HCID 122930102-Bromo-1,1-dimethoxypropaneHCID 58191769HCID 58191769, compound

Product 1

HCID 58191758HCID 58191758, compound

Reagents, catalysts & solvents 3

HCID 280Carbon DioxideSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

To a solution of (1) (8.86 g, 36.2 mmole) in 250 mL of anhydrous THF in a 3-neck flamed dried round bottom flask at −70° C. (acetone-dry ice bath) is slowly added the Grignard reagent prepared from bromopropionaldehyde dimethyl acetal (16.5 g, 90.4 mmol) and Mg turnings (4.39 g, 181 mmol) in anhydrous THF (250 mL), maintaining internal temperature around −68° C. to −70° C. After stirring at −70° C. for 2 hours, the reaction mixture is diluted with 200 mL of water with the dry ice bath removed. The mixture is poured into a separatory funnel, and the mixture is extracted 3 times with ethyl acetate (150 mL). The organic layers are combined and dried over Na2SO4 and the solvent evaporated leaving a thick yellow oil (11 g, 100% crude yield, MS ES+258.02).

Workup

  1. dry with materialdried round bottom flask at −70° C. (acetone-dry ice bath)
  2. additionis slowly added the Grignard reagent
  3. temperaturemaintaining internal temperature around −68° C. to −70° C
  4. customremoved
  5. additionThe mixture is poured into a separatory funnel
  6. extractionthe mixture is extracted 3 times with ethyl acetate (150 mL)
  7. dry with materialdried over Na2SO4
  8. customthe solvent evaporated
  9. customleaving a thick yellow oil (11 g, 100% crude yield, MS ES+258.02)

Sources & evidence

ORD record
ord-d8ff1ddedfab43ce9b6a87c6f593fc61
Source dataset
uspto-grants-2013_10
Patent number
US08546336B2

Reaction notes

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