Tetrahydrofuran → HCID 178524980, compound

HRID 1609708Notes

Reaction equation

HRID 1609708 reaction equation
[CH2:1]1[C@:6]2([OH:10])[C:7]([O:9][C@@H:4]([CH2:5]2)[C@@H:3]([OH:11])[C@H:2]1[OH:12])=[O:8].C1C[O:16]CC1>Cl>[CH2:5]1[C@@H:4]([OH:9])[C@@H:3]([OH:11])[C@H:2]([OH:12])[CH2:1][C@@:6]1([C:7]([OH:16])=[O:8])[OH:10]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 101711082HCID 101711082, compound

Product 1

HCID 178524980HCID 178524980, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 10 g (9.6 mmol) 1,4-O-dicarbotrichloroethoxy-3-O-dicarbotrichloroethoxycaffeoyl quinide is stirred for 5 days at ambient temperature in 65 ml THF and 8 ml concentrated HCl. After separation of the THF and saturation with NaCl, the aqueous phase is extracted with 3×40 ml ethyl acetate. The combined extracts are then washed with brine and dried over sodium sulfate and the solvent is evaporated. Treatment of the residue with a mixture of 1 volume dichloromethane to 10 volumes hexane gives 9.5 g 1,4-O-dicarbotrichloroethoxy-3-O-dicarbotrichloroethoxycaffeoyl quinic acid (yield 93%) in the form of an amorphous solid.

Workup

  1. customAfter separation of the THF and saturation with NaCl
  2. extractionthe aqueous phase is extracted with 3×40 ml ethyl acetate
  3. washThe combined extracts are then washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated
  6. additionTreatment of the residue with a mixture of 1 volume dichloromethane to 10 volumes hexane

Sources & evidence

ORD record
ord-8c0a19aeb60349359dcc2d29a0912c12
Source dataset
uspto-grants-1995_03
Patent number
US05401858

Reaction notes

Loading…