Ethylene Glycol → 8,8-Difluoro-6-iodo-1,4-dioxaspiro[4.5]dec-6-ene

HRID 337857Notes

Reaction equation

HRID 337857 reaction equation
[F:1][C:2]1([F:10])[CH2:7][CH2:6][C:5](=[O:8])[C:4]([I:9])=[CH:3]1.[CH2:11](O)[CH2:12][OH:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[F:1][C:2]1([F:10])[CH2:7][CH2:6][C:5]2([O:13][CH2:12][CH2:11][O:8]2)[C:4]([I:9])=[CH:3]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 899630934,4-Difluoro-2-iodocyclohex-2-en-1-one

Product 1

HCID 899628608,8-Difluoro-6-iodo-1,4-dioxaspiro[4.5]dec-6-ene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 67a by using the 4,4-difluoro-2-iodocyclohex-2-en-1-one (1.46 g, 5.66 mmol) prepared in Example 88c, ethylene glycol (750 mg, 12.1 mmol), p-toluenesulfonic acid hydrate (60 mg, 0.31 mmol) and benzene (30 mL), to yield a mixture of the title compound and a by-product.

Workup

  1. customThe reaction and aftertreatment
  2. customto yield

Sources & evidence

ORD record
ord-ba2b597e077a47bdb3f4cfb45b79031e
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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