Ethanol → HCID 20070567, compound

HRID 981715Notes

Reaction equation

HRID 981715 reaction equation
[Mg].C(O)C.[C:5]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])[CH2:6][C:7]([CH3:9])=[O:8].[CH2:16]([S:23][CH2:24][CH2:25][C:26](Cl)=[O:27])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.OS(O)(=O)=O>C(OCC)C.C(Cl)(Cl)Cl>[CH2:16]([S:23][CH2:24][CH2:25][C:26](=[O:27])[CH:6]([C:5]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:7](=[O:8])[CH3:9])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 5

HCID 702EthanolHCID 1118Sulfuric AcidHCID 15538Tert-butyl acetoacetateHCID 5462224MagnesiumHCID 20070573HCID 20070573, compound

Product 1

HCID 20070567HCID 20070567, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6212ChloroformSolvent

Conditions

Temperature
12 °C

Procedure

10.7 g (0.44 mol) of magnesium, 2 ml of chloroform and 46 g (1 mol) of absolute ethanol are initially placed, with the exclusion of moisture, in a 1 1 flask equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser, and are heated under reflux for 1 hour, with stirring. 300 ml of diethyl ether are then added dropwise and the mixture is stirred for 1.5 hours. The mixture is then cooled to approx. 12° C. 63.2 g (0.4 mol) of tert-butyl acetoacetate are added dropwise at this temperature. The reaction mixture is cooled further to approx. -3° C., and 85.8 g (0.4 mol) of benzylthiomethylacetyl chloride in 100 ml of absolute diethyl ether are added dropwise at this temperature in the course of 45 minutes. The mixture is then stirred for a further hour at approx. -3° C. and is then stirred for a further 2 hours without cooling, in the course of which it reaches room temperature. The reaction mixture is stirred into 400 g of ice-water and 48 g of concentrated H2SO4. The organic phase is separated off and is washed with 150 ml of water, 100 ml of bicarbonate and 150 ml of water again and is then dried and concentrated.

Workup

  1. customequipped with a stirrer
  2. temperaturea thermometer, a dropping funnel and a reflux condenser, and are heated
  3. temperatureunder reflux for 1 hour
  4. stirringthe mixture is stirred for 1.5 hours
  5. temperatureThe reaction mixture is cooled further to approx. -3° C.
  6. stirringThe mixture is then stirred for a further hour at approx. -3° C.
  7. stirringis then stirred for a further 2 hours
  8. temperaturewithout cooling, in the course of which it
  9. customreaches room temperature
  10. customThe organic phase is separated off
  11. washis washed with 150 ml of water, 100 ml of bicarbonate and 150 ml of water again
  12. customis then dried
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-f84f213dbc114e10a48f5b5b12389330
Source dataset
uspto-grants-1991_02
Patent number
US04992504

Reaction notes

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