Citric Acid → HCID 178472501, compound

HRID 1968942Notes

Reaction equation

HRID 1968942 reaction equation
Cl[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[OH:9][CH:10]1[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]1.N1C=CN=C1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[CH3:6][C:5]([Si:2]([CH3:4])([CH3:3])[O:9][C@H:10]1[CH2:11][CH2:12][C@H:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:15]1)([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 86973Ethyl 4-hydroxycyclohexanecarboxylate

Product 1

HCID 178472501HCID 178472501, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Chloro(1,1-dimethylethyl)dimethylsilane (115 g; 0.76 mol) was added in portions over 1 hour to a solution of commercially available ethyl 4-hydroxycyclohexanecarboxylate (118 g; 0.68 mol), imidazole (103 g; 1.52 mol) and dimethylformamide (400 mL) stirred under an atmosphere of argon. A small exotherm was observed resulting in the reaction mixture temperature increasing to ˜40° C. The mixture was stirred at room temperature overnight then poured into 10% citric acid solution (2 L) and extracted with diethyl ether (2×800 mL). The ether extracts were washed with water, brine and then dried (Na2SO4) and the solvent was removed to give the title compound as an oil (198.4 g)

Workup

  1. customA small exotherm was observed resulting in the reaction mixture temperature
  2. stirringThe mixture was stirred at room temperature overnight
  3. extractionextracted with diethyl ether (2×800 mL)
  4. washThe ether extracts were washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-c7ad5c44b5ec4e12b6ab0641c5e8de22
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

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