Thionyl Chloride → HCID 10900314, compound

HRID 1457982Notes

Reaction equation

HRID 1457982 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:9](O)([CH3:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].S(Cl)(Cl)=O>N1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1(/[C:9](/[CH3:16])=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:8]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 11010183HCID 11010183, compound

Product 1

HCID 10900314HCID 10900314, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 90.31 g (0.37 mol) portion of ethyl 1-ethoxycarbonyl-β-hydroxy-β-methyl-cyclopropanepropanoate was dissolved in 182 ml of pyridine to which was subsequently added dropwise thionyl chloride at -10° C. to -5° C. After completion of the dropwise addition, this was stirred at the same temperature for 3 hours. After completion of the reaction, the reaction solution was poured into 1 liter of ice water and extracted with dichloromethane (300 ml×3). The organic layers were combined, washed with 1N hydrochloric acid (1 liter×1) and saturated brine (1 liter×1) in that order and then dried on anhydrous sodium sulfate. To the resulting dichloromethane solution was added dropwise 58 ml of 1,8-diazabicyclo[5,4,0]-7-undecene at 0° C., followed by 18 hours of stirring at room temperature. After completion of the reaction, the reaction solution was washed with 1N hydrochloric acid (1 liter×1) and saturated brine (1 liter×1) in that order, and then dried over anhydrous sodium sulfate. After evaporation of the solvent, the resulting residue was applied to a silica gel column chromatography to yield 56.57 g (68%) of the title compound as an oily substance from the eluate of n-hexane:ethyl acetate=9:1.

Workup

  1. additionAfter completion of the dropwise addition
  2. customAfter completion of the reaction
  3. extractionextracted with dichloromethane (300 ml×3)
  4. washwashed with 1N hydrochloric acid (1 liter×1) and saturated brine (1 liter×1) in that order
  5. dry with materialdried on anhydrous sodium sulfate
  6. additionTo the resulting dichloromethane solution was added dropwise 58 ml of 1,8-diazabicyclo[5,4,0]-7-undecene at 0° C.
  7. waitfollowed by 18 hours
  8. stirringof stirring at room temperature
  9. customAfter completion of the reaction
  10. washthe reaction solution was washed with 1N hydrochloric acid (1 liter×1) and saturated brine (1 liter×1) in that order
  11. dry with materialdried over anhydrous sodium sulfate
  12. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-4d9d7940f3234d7986f71dd8e318c557
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

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