N-bromobutanimide → Ethyl 3-cyclopropyl-2-oxopropanoate

HRID 1689752Notes

Reaction equation

HRID 1689752 reaction equation
C1C(=O)N(Br)C(=[O:4])C1.[CH2:9]([O:11][C:12]([C:14]1([CH2:20][CH:21]2[CH2:23][CH2:22]2)SCCCS1)=[O:13])[CH3:10].CCCCCC.C(Cl)Cl>C(#N)C.O>[CH2:9]([O:11][C:12](=[O:13])[C:14](=[O:4])[CH2:20][CH:21]1[CH2:23][CH2:22]1)[CH3:10]

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 21226440Methylenechloride HexaneHCID 22285400Ethyl 2-(cyclopropylmethyl)-1,3-dithiane-2-carboxylate

Product 1

HCID 22285629Ethyl 3-cyclopropyl-2-oxopropanoateYield 61.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a 0° C. suspension of NBS (439 mmol, 79 g) in a mixture of acetonitrile (400 mL) and water (100 mL) is added a solution of 2-cyclopropylmethyl-[1,3]dithiane-2-carboxylic acid ethyl ester (73.2 mmol, 18.05 g) in acetonitrile (50 mL) over 15 minutes. The reaction is warmed and stirred at room temperature. After 45 minutes, 500 mL of 1:1 hexane/DCM is added. The layers are separated. The organic layer is washed with saturated Na2SO3 (2×225 mL) and brine (2×225 mL), dried with Na2SO4, filtered, and concentrated under reduced pressure to a residue. The residue is diluted in CCl4 and filtered. The filtrate is concentrated to give the title compound (7 g, 61%). LC-ES/MS: 157.0 (M+1).

Workup

  1. temperatureThe reaction is warmed
  2. customThe layers are separated
  3. washThe organic layer is washed with saturated Na2SO3 (2×225 mL) and brine (2×225 mL)
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to a residue
  7. additionThe residue is diluted in CCl4
  8. filtrationfiltered
  9. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-c0c3f2888607420cbbfdf5bb6d7d107d
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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