2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 4-((tert-Butyl(dimethyl)silyl)oxy)cyclopent-2-en-1-one

HRID 2163169Notes

Reaction equation

ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[O:15]([CH:23]1[CH2:27][CH:26]([OH:28])[CH:25]=[CH:24]1)[Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>O1CCOCC1>[O:15]([CH:23]1[CH2:27][C:26](=[O:28])[CH:25]=[CH:24]1)[Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 55 °C

Procedure

1.13 grams of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) was dissolved in 15 milliliters of dioxane, to which was then added 660 milligrams of crude 4-t-butyldimethylsiloxycyclopent-2-en-1-ol (purity 74%), after which the mixture was heated at 55° C. for 16 hours with stirring. After completion of the reaction, the precipitate separating out was filtered off. When the filtrate was concentrated under reduced pressure, 2.0 grams of a crude product was obtained.

Workup

customAfter completion of the reaction
customthe precipitate separating out
filtrationwas filtered off
concentrationWhen the filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-7e03292ba69b400f98995913705f1951
Source dataset: uspto-grants-1979_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04132726

Reaction notes

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