p-Chlorothiophenol → HCID 15050275, compound

HRID 2059862Notes

Reaction equation

HRID 2059862 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:16][C:17](=[O:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C=O)C.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:16][C:17](=[O:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 15050275HCID 15050275, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of 4-chlorobenzenethiol (1.75 g, 12.15 mmol) and K2CO3 (3.36 g, 24.30 mmol) in DMF (40 mL) was added ethyl 4-chloro-3-oxobutanoate (2.0 g, 12.15 mmol). The mixture was stirred at RT for 18 hours, diluted with saturated NaHCO3 (40 mL) and extracted with EtOAc (50 mL). The EtOAc layer was dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (silica gel/hexane-EtOAc 100:0 to 0:100 gradient, using LC-MS to identify fractions containing the desired product) to afford ethyl 4-(4-chlorophenylthio)-3-oxobutanoate 10A (2.07 g, 59% yield). 1H NMR (500 MHz, Chloroform-D) δ ppm 7.22-7.32 (4H, m), 4.18 (2H, q, J=7.15 Hz), 3.79 (2H, s), 3.62 (2H, s), 1.27 (3H, t, J=7.01 Hz).

Workup

  1. extractionextracted with EtOAc (50 mL)
  2. dry with materialThe EtOAc layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography (silica gel/hexane-EtOAc 100:0 to 0:100 gradient
  5. additioncontaining the desired product)

Sources & evidence

ORD record
ord-8d554c5b2959457b877a462b94f32faa
Source dataset
uspto-grants-2012_10
Patent number
US08278316B2

Reaction notes

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