HCID 54205606, compound → HCID 22337820, compound

HRID 585723Notes

Reaction equation

HRID 585723 reaction equation
[Si]([O:8][C:9]1[CH:14]=[C:13]([O:15][Si](C(C)(C)C)(C)C)[CH:12]=[CH:11][C:10]=1[CH:23]1[CH2:28][CH2:27][C:26]([OH:34])([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25][CH2:24]1)(C(C)(C)C)(C)C>CO>[OH:8][C:9]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:10]=1[CH:23]1[CH2:28][CH2:27][C:26]([OH:34])([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25][CH2:24]1

Participants

3

Reactant 1

HCID 54205606HCID 54205606, compound

Product 1

HCID 22337820HCID 22337820, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the other isomer of ethyl 4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1-hydroxycyclohexanecarboxylate (25 mg, 0.05 mmol) in methanol (2 ml) was stirred rapidly with Amberlyst A-26 (100 mg) for 18 hr. After this time the reaction mixture was filtered. The resin was then stirred rapidly for 1 hr in a solution of methanol (2 ml) and glacial acetic acid (5 drops). The reaction mixture was filtered and the combined filtrates concentrated in vacuo. Purification via flash column chromatography (SiO2, ethyl acetate/petrol, 2:1) afforded the title compound (5 mg, 34%) as a white solid. δH (d4-MeOH) 1.22 (3H, t), 1.40-1.54 (4H, m), 1.63-1.74 (2H, m), 2.18-2.25 (2H, m), 2.68-2.78 (1H, m), 4.14 (2H, q), 6.11 (1H, dd), 6.15 (1H, d), 6.71 (1H, d); m/z (ES−) 279 (M−H)−.

Workup

  1. filtrationAfter this time the reaction mixture was filtered
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe combined filtrates concentrated in vacuo
  4. customPurification via flash column chromatography (SiO2, ethyl acetate/petrol, 2:1)

Sources & evidence

ORD record
ord-6476d05c80ee481792f452bfa9738a96
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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