HCID 22337768, compound → HCID 22337766, compound

HRID 2307172Notes

Reaction equation

HRID 2307172 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-04428b7f17464fd9ae6445460883ff98
Source dataset
uspto-grants-2004_12
Patent number
US06828460B2

Reaction notes

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