Methanol → Methyl 2,2-dimethyl-6-[(4-phenyl-2-quinolyl)thio]-hexanoate

HRID 2396518Notes

Reaction equation

HRID 2396518 reaction equation
[CH3:1][C:2]([CH3:12])([CH2:7][CH2:8][CH2:9][CH2:10][SH:11])[C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].Cl[C:16]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1.CO>CN(C)C=O>[CH3:1][C:2]([CH3:12])([CH2:7][CH2:8][CH2:9][CH2:10][S:11][C:16]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 23066872-Chloro-4-phenylquinolineHCID 15681404Methyl 2,2-dimethyl-6-mercaptohexanoate

Product 1

HCID 10318437Methyl 2,2-dimethyl-6-[(4-phenyl-2-quinolyl)thio]-hexanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4 g of methyl 2,2-dimethyl-6-mercaptohexanoate in 100 cc of dimethylformamide, is added 0.55 g of sodium hydride (50% w/w dispersion in mineral oil). The mixture is stirred for 2 hours until effervescence has stopped. A solution of 5 g of 2-chloro-4-phenylquinoline in 50 cc of dimethyl-formamide is then added. The obtained mixture is heated to 60 C. for 8 hours. After cooling, 10 cc of methanol is added and the mixture evaporated. The resultant residue is purified by flash chromatography on silica gel (30-60 mm; eluent: 8:2 hexane/ethyl acetate) to give methyl 2,2-dimethyl-6-[(4-phenyl-2-quinolyl)thio]-hexanoate is obtained as an oil.

Workup

  1. temperatureThe obtained mixture is heated to 60 C
  2. waitfor 8 hours
  3. temperatureAfter cooling
  4. customthe mixture evaporated
  5. customThe resultant residue is purified by flash chromatography on silica gel (30-60 mm; eluent: 8:2 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-23144e7c724a4dbaa012d25b027155a3
Source dataset
uspto-grants-1996_02
Patent number
US05492915

Reaction notes

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