4-Ethylbenzyl chloride → 5-[(4-ethylbenzyl)sulfanyl]-3-(methoxymethoxy)-1-(methoxymethyl)pyridin-2(1H)-one

HRID 709032Notes

Reaction equation

HRID 709032 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:10](=[O:11])[N:9]([CH2:12][O:13][CH3:14])[CH:8]=[C:7]([S:15][CH2:16][CH2:17][C:18](OC)=O)[CH:6]=1.CC(C)([O-])C.[K+].Cl[CH2:29][C:30]1[CH:35]=[CH:34]C(CC)=[CH:32][CH:31]=1>C1COCC1>[CH2:35]([C:30]1[CH:29]=[CH:18][C:17]([CH2:16][S:15][C:7]2[CH:6]=[C:5]([O:4][CH2:3][O:2][CH3:1])[C:10](=[O:11])[N:9]([CH2:12][O:13][CH3:14])[CH:8]=2)=[CH:32][CH:31]=1)[CH3:34]

Participants

5

Reactant 3

HCID 738434-Ethylbenzyl chlorideHCID 23665647Potassium tert-butoxideHCID 86731526Methyl 3-((5-(methoxymethoxy)-1-(methoxymethyl)-6-oxo-1,6-dihydropyridin-3-yl)thio)propanoate2×

Product 1

HCID 867315275-[(4-ethylbenzyl)sulfanyl]-3-(methoxymethoxy)-1-(methoxymethyl)pyridin-2(1H)-oneYield 79.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-{[5-(methoxymethoxy)-1-(methoxymethyl)-6-oxo-1,6-dihydropyridin-3-yl]sulfanyl}propanoate (Intermediate 16) (290 mg, 0.91 mmol) in THF (5 ml) at −45° C. was added potassium tert-butoxide (113 mg, 1.01 mmol) and the resulting mixture allowed to stir for 20 minutes. 1-(Chloromethyl)-4-ethylbenzene (170 mg, 1.10 mmol) was then added and the reaction mixture allowed to warm to room temperature and stirred for 4 hours before being quenched with water and extracted into dichlormethane. The combined organics were concentrated and subjected to column chromatography (SiO2; 0-10% methanol in dichloromethane) to yield 5-[(4-ethylbenzyl)sulfanyl]-3-(methoxymethoxy)-1-(methoxymethyl)pyridin-2(1H)-one (253 mg, 79%).

Workup

  1. stirringstirred for 4 hours
  2. custombefore being quenched with water
  3. extractionextracted into dichlormethane
  4. concentrationThe combined organics were concentrated

Sources & evidence

ORD record
ord-0cd9ac3333f2486483907dcee3035191
Source dataset
uspto-grants-2015_11
Patent number
US09180122B2

Reaction notes

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