Dimethyl Sulfoxide → HCID 13527237, compound

HRID 493176Notes

Reaction equation

HRID 493176 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=O.[C:12]([O-])([O-])=[O:13].[K+].[K+].[C:18]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:19][SH:20].[CH3:25][S:26]([CH3:28])=[O:27]>>[CH2:23]([O:22][C:18]([C:19]1[S:20][C:2]2[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=2[CH:4]=1)=[O:21])[CH3:24].[CH2:23]([O:22][C:18](=[O:21])[CH2:25][S:26]([C:3]1[CH:6]=[C:7]([O:10][CH3:11])[C:8]([O:13][CH3:12])=[CH:9][C:2]=1[F:1])([OH:27])[CH3:28])[CH3:24]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 27348722-Fluoro-5-methoxybenzaldehyde

Product 2

HCID 13527237HCID 13527237, compoundHCID 68725746HCID 68725746, compound

Conditions

Temperature
50 °C

Procedure

To a solution of 2-fluoro-5-methoxybenzaldehyde (21.70 g, 141 mmol) in 280 mL of DMSO were successively added K2CO3 (21.4 g, 1.1 eq.) and ethyl thioglycolate (17.07 mL, 1.1 eq.), and the mixture was vigorously stirred at 50° C. for 5 h. After cooling, the reaction mixture was poured onto crashed ice/HCl, twofold extracted with AcOEt, washed with water and brine, dried over magnesium sulfate, and evaporated. Flash chromatography (SiO2, hexane/AcOEt=85/15) yielded in the less polar fractions 6.40 g of the title compound as light yellow solid and in the more polar ones 19.27 g of [(2-fluoro-4,5-Dimethoxy-phenyl)-hydroxy-methylsulfanyl]-acetic acid ethyl ester which can be recycled by stirring over night at 70° C. in DMSO in the presence of K2CO3.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured
  3. extractiontwofold extracted with AcOEt
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-4a2836f106da4a2eb1354fd6791fe372
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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