HCID 22337803, compound → HCID 22337769, compound

HRID 585714Notes

Reaction equation

HRID 585714 reaction equation
COC[O:4][C:5]1[CH:10]=[C:9]([O:11]COC)[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:20][CH2:19][CH2:18][C:17]([CH2:22][OH:23])([OH:21])[CH2:16]1>CO>[OH:21][C:17]1([CH2:22][OH:23])[CH2:18][CH2:19][CH2:20][CH:15]([C:6]2[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:5]=2[OH:4])[CH2:16]1

Participants

3

Reactant 1

HCID 22337803HCID 22337803, compound

Product 1

HCID 22337769HCID 22337769, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(±)-3-[2,4-Bis(methoxymethoxy)phenyl]-1-(hydroxymethyl)cyclohexanol (29 mg), methanol (2 ml) and acidic ion exchange resin (300 mg) were heated under reflux for 3 hr. 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 furnish the title compound as a cream solid (5 mg, 24%). δH (CD3OD) 1.20-2.00 (8H, m), 2.89 (1H, tt), 3.61 (1H, d), 3.69 (1H, d), 6.20-6.26 (2H, m), 6.90 (1H, d); m/z (ES−) 237 (M−H)−.

Workup

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

Sources & evidence

ORD record
ord-6d93774ff87f447e980e5c8989364b8d
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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