Pyridine → HCID 13518917, compound

HRID 65260Notes

Reaction equation

HRID 65260 reaction equation
[SH:1][CH2:2][CH:3]1[CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][O:6][C:4]1=[O:5].[CH2:15]([C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)[CH2:16][CH2:17][CH3:18].N1C=CC=CC=1>C(OCC)C>[CH2:15]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([S:1][CH2:2][CH:3]2[CH:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:7][O:6][C:4]2=[O:5])=[O:24])=[CH:26][CH:27]=1)[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1200494-Butylbenzoyl chlorideHCID 13518975alpha-Mercaptomethyl-beta-phenyl-gamma-butyrolactone

Product 1

HCID 13518917HCID 13518917, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 1.5 g of α-mercaptomethyl-β-phenyl-γ-butyrolactone in 30 ml of ethyl ether were added at room temperature 4.3 g of p-n-butylbenzoyl chloride and then 1.9 ml of pyridine. The mixture was kept at room temperature for 2.5 hours. After completion of the reaction, the reaction mixture was diluted with 100 ml of ethyl ether, washed with 10% hydrochloric acid, 10% aqueous sodium hydrogen carbonate and then satureated saline, dried over magnesium sulfate and the solvent was distilled off. The crude product thus obtained was purified by a silica gel column chromatography to give 2.1 g (yield 79%) of the title compound.

Workup

  1. customAfter completion of the reaction
  2. washwashed with 10% hydrochloric acid, 10% aqueous sodium hydrogen carbonate
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe crude product thus obtained
  6. customwas purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-2fed1269505b4a02ba1545817fd2479d
Source dataset
uspto-grants-1986_09
Patent number
US04613613

Reaction notes

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