Chlorosuccinimide → HCID 66783566, compound

HRID 1096814Notes

Reaction equation

HRID 1096814 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH:5]=[N:6][OH:7].[C:8]([Sn:10]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH2:13][CH3:14])#[CH:9].ClN1C(=O)CCC1=O>C(Cl)Cl>[CH2:19]([Sn:10]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:11][CH2:12][CH2:13][CH3:14])[C:8]1[O:7][N:6]=[C:5]([CH2:4][CH2:3][CH2:2][OH:1])[CH:9]=1)[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 621176EthynyltributyltinHCID 85819537HCID 85819537, compound

Product 1

HCID 66783566HCID 66783566, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Hydroxybutyraldehyde oxime (Paul, R.; Fluchaire, M.; Collardeau, G. Bull. Soc. Chim. France, 1950, 668; 11.5 g, 112 mmol) was dissolved in CH2Cl2 (600 mL). KHCO3 (16.8 g, 168 mmol), then ethynyltributyltin (35.3 g, 112 mmol), then N-chlorosuccinimide (16.4 g, 123 mmol) were added, and the mixture was stirred at rt overnight. The mixture was washed with brine. The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 1:5→1:4→1:3→1:2→1:1) yielded the title compound (13.0 g, 28%). LC-MS: tR=1.17, ES+: 418.20.

Workup

  1. washThe mixture was washed with brine
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the residue by FC (EtOAc/heptane 1:5→1:4→1:3→1:2→1:1)

Sources & evidence

ORD record
ord-2d77d09efaec4bcf8841e1cb407873de
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

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