Acetic Acid → 4-Methoxybenzyl 2-(acetoxymethyl)-5-(hydroxymethyl)benzoate

HRID 1766857Notes

Reaction equation

[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C.[C:23]([O:26][CH2:27][C:28]1[CH:45]=[CH:44][C:43]([CH2:46][O:47][Si](C(C)(C)C)(C)C)=[CH:42][C:29]=1[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)=[O:31])(=[O:25])[CH3:24]>O1CCCC1>[C:23]([O:26][CH2:27][C:28]1[CH:45]=[CH:44][C:43]([CH2:46][OH:47])=[CH:42][C:29]=1[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)=[O:31])(=[O:25])[CH3:24]

Participants

Conditions

Temperature: 50 °C

Procedure

Tetrabutylammonium fluoride (1N tetrahydrofuran solution; 9.9 ml, 9.9 mmol) and acetic acid (592.9 mg, 9.87 mmol) were added to a solution of 4-methoxybenzyl 2-(acetoxymethyl)-5-[(tert-butyldimethylsilyl)oxymethyl]benzoate (905 mg, 1.97 mmol) obtained from Example 1-(8) in tetrahydrofuran (5 ml). The mixture was stirred at 50° C. for 1 hour, and then the solvent was distilled off under reduced pressure. The oily residue was subjected to chromatography on a silica gel (25 g) column (eluent; ethyl acetate:hexane=1:1) to give the title compound (500.1 mg, 74% yield) as a colorless amorphous solid.

Workup

distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-b39089debba64ff0aca33c95736cf2d5
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07230023B2

Reaction notes

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