Ethylene Glycol → HCID 90004235, compound

HRID 587855Notes

Reaction equation

HRID 587855 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C@@H:4]([C:12]([O:14][CH3:15])=[O:13])[CH2:3]1.[CH2:16](O)[CH2:17][OH:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[C:2]12([O:18][CH2:17][CH2:16][O:1]1)[C:11]1[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH2:5][C@@H:4]([C:12]([O:14][CH3:15])=[O:13])[CH2:3]2

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 90004151HCID 90004151, compound

Product 1

HCID 90004235HCID 90004235, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of (R)-methyl 4-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate (4.5 g, 22.03 mmol) in benzene (40 mL), ethane-1,2-diol (3.69 mL, 66.1 mmol) and a catalytic amount of p-toluenesulfonic acid was added. The reaction mixture was heated to reflux temperature and further maintained for 20 hours. Then, reaction mixture was allowed to RT, concentrated under vacuum to yield 12 g of crude compound. This crude material was purified by flash chromatography (Biotage) using 7% ethyl acetate in hexane to give title compound (4.7 g) m/z 248.6.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux temperature
  3. temperaturefurther maintained for 20 hours
  4. customThen, reaction mixture
  5. customwas allowed to RT
  6. concentrationconcentrated under vacuum
  7. customto yield 12 g of crude compound
  8. customThis crude material was purified by flash chromatography (Biotage)

Sources & evidence

ORD record
ord-b062345ac2b84edc9e53292be7d28b55
Source dataset
uspto-grants-2016_01
Patent number
US09227919B2

Reaction notes

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