Acetic Anhydride → 2-(4-Acetoxybenzyl)-3-ethylmaleic anhydride

HRID 1774378Notes

Reaction equation

[Si]([O:8][C:9]1[CH:26]=[CH:25][C:12]([CH2:13][CH:14]([C:22]([OH:24])=[O:23])[C:15]([CH2:20][CH3:21])(O)[C:16]([OH:18])=O)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[C:27](OC(=O)C)(=[O:29])[CH3:28]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:27]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][C:14]2[C:22]([O:23][C:16](=[O:18])[C:15]=2[CH2:20][CH3:21])=[O:24])=[CH:25][CH:26]=1)(=[O:29])[CH3:28]

Participants

Conditions

Temperature: 115 °C

Procedure

To the crude 3-(4-t-butyldimethylsilyloxybenzyl)-2-ethyl-2-hydroxysuccinic acid thus obtained was added acetic anhydride (5 mL), and the mixture was stirred at 115° C. for 3 h. The acetic anhydride was evaporated under reduced pressure, and the residue thus obtained was subjected to silica gel column chromatography (toluene-ethyl acetate 19:1→16:1) to give the title compound as oil in an amount of 210 mg (2 step yield: 79%).

Workup

customThe acetic anhydride was evaporated under reduced pressure
customthe residue thus obtained

Sources & evidence

ORD record: ord-6027c8cefc4a4ed8a77d32a47355d587
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260375B2

Reaction notes

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