HCID 22337768, compound → HCID 22337766, compound

HRID 585711Notes

Reaction equation

HRID 585711 reaction equation
[F:1][C:2]1([F:22])[CH2:7][CH2:6][CH2:5][CH:4]([C:8]2[CH:13]=[CH:12][C:11]([O:14]COC)=[CH:10][C:9]=2[O:18]COC)[CH2:3]1>CO>[F:1][C:2]1([F:22])[CH2:7][CH2:6][CH2:5][CH:4]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=2[OH:18])[CH2:3]1

Participants

3

Reactant 1

HCID 22337768HCID 22337768, compound

Product 1

HCID 22337766HCID 22337766, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (±)-1-(3,3-difluorocyclohexyl)-2,4-bis(methoxymethoxy)benzene (30 mg), methanol (2 ml) and acidic ion exchange resin (200 mg) was heated under reflux for 4 h. The reaction mixture was filtered and the resin was washed with methanol. The combined filtrate and washings were evaporated in vacuo and the crude residue was purified by preparative HPLC to give the title compound as a solid (5 mg, 23%). δH (CD3OD) 1.2-2.2 (8H, m), 3.08 (1H, m), 6.23-6.27 (2H, m), 6.87 (1H, d); m/z (ES−) 287 (M−1+AcOH)−.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. filtrationThe reaction mixture was filtered
  4. washthe resin was washed with methanol
  5. customThe combined filtrate and washings were evaporated in vacuo
  6. customthe crude residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-7d88544dc1604ebc8299a4d802237f9e
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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