Water → HCID 69588342, compound

HRID 1897009Notes

Reaction equation

HRID 1897009 reaction equation
Cl[CH:2]([C:8]([CH3:10])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(=O)([O-])O.[Na+].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([SH:23])=[CH:19][CH:18]=1.O>COCCOC>[CH2:6]([O:5][C:3](=[O:4])[CH:2]([S:23][C:20]1[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=1)[C:8](=[O:9])[CH3:10])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 7815p-ChlorothiophenolHCID 11858Ethyl 2-chloroacetoacetateHCID 516892Sodium Bicarbonate

Product 1

HCID 69588342HCID 69588342, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of ethyl 2-chloroacetoacetate (1.58 g, 9.61 mmol) in ethylene glycol dimethyl ether (30 mL) was added sodium hydrogencarbonate (ca. 15 g) and 4-chlorothiophenol (1.39 g, 9.61 mmol). The suspension was heated to reflux and stirred for 3 hours. The reaction mixture was allowed to cool to room temperature, and water (100 mL) was added. The mixture was extracted with ethyl ether (75 mL), and the organic extract was washed with brine (150 mL). The organic phase was dried (magnesium sulfate), filtered, and concentrated to afford a yellow oil. Flash chromatography over silica (ethyl acetate/hexanes) provided 1.44 g (55%) of the product as a colorless oil: 1H NMR (CDCl3) δ 13.8 (s, 1H), 7.26-7.21 (m, 2H), 7.06-7.04 (m, 2H), 4.21 (q, J=7.1 Hz, 2H), 2.33 (s, 3H), 1.20 (t, J=7.1 Hz, 3H).

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux
  3. extractionThe mixture was extracted with ethyl ether (75 mL)
  4. extractionthe organic extract
  5. washwas washed with brine (150 mL)
  6. dry with materialThe organic phase was dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a yellow oil

Sources & evidence

ORD record
ord-4634b88f3b4d4c40ad4946fe2c7f2eed
Source dataset
uspto-grants-2013_08
Patent number
US08518999B2

Reaction notes

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