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

HRID 2261730Notes

Reaction equation

HRID 2261730 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 is 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 is filtered. The filtrate is concentrated to give the title compound (7 g, 61%). LC-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. filtrationis filtered
  9. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-1ae2d0e3f2fc4bcd8b36543131a01205
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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