Chlorosuccinimide → Chloro[1-(4-methoxyphenyl)cyclopropyl]acetaldehyde

HRID 500110Notes

Reaction equation

HRID 500110 reaction equation
N1CCC[C@H]1C(O)=O.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2([CH2:20][CH:21]=[O:22])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1.[Cl:23]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Cl:23][CH:20]([C:17]1([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[CH2:19][CH2:18]1)[CH:21]=[O:22]

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 145742L-ProlineHCID 86621501[1-(4-Methoxyphenyl)cyclopropyl]acetaldehyde

Product 1

HCID 86621500Chloro[1-(4-methoxyphenyl)cyclopropyl]acetaldehyde

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

L-Proline (10 mg, 0.1 mmol) was added to a solution of [1-(4-methoxyphenyl)cyclopropyl]acetaldehyde (100 mg, 0.53 mmol) in chloroform (1 mL) at 0° C. followed by addition of N-chlorosuccinimide (84 mg, 0.63 mmol). The reaction mixture was stirred at ambient temperature for 2 h. The mixture was diluted with hexanes and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography eluting with ethyl acetate in hexanes (0-10%) to afford the desired product.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by flash chromatography
  4. washeluting with ethyl acetate in hexanes (0-10%)

Sources & evidence

ORD record
ord-6339feab97db480994be8e84a3fbe87e
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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