Hydroquinone → HCID 69853448, compound

HRID 987924Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]([CH2:20][CH:21]=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[O:10][C:9]1([CH3:29])[CH3:28])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:30]1([CH:37]=CC(O)=[CH:33][CH:32]=1)O.C=CC=C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]([CH2:20][CH:21]2[CH:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:33][CH:32]=[CH:30][CH2:37]2)[O:10][C:9]1([CH3:28])[CH3:29])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 4-benzyl-5-(3-ethoxycarbonyl-allyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (6.55 g) in toluene (50 ml) was placed in a stainless steel bomb equipped with a PTFE liner. Hydroquinone (350 mg) was added, and the vessel cooled to −78° C. 1,3-butadiene (100 g) was condensed into the vessel, which was then sealed and heated to 150° C. for 16 hours. After cooling, the vessel was opened and the contents removed and evaporated to dryness. The residue was subjected to flash chromatography on silica gel eluting with hexane/ethyl acetate (95:5) to afford 4-benzyl-5-(6-ethoxycarbonyl-cyclohex-3-enylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (2.54 g, 34%) as a mixture of trans isomers (mass spectrum 458 [M+H]+) together with recovered starting material (2.17 g, 33%).

Workup

customcondensed into the vessel, which
customwas then sealed
temperatureheated to 150° C. for 16 hours
temperatureAfter cooling
customthe contents removed
customevaporated to dryness

Sources & evidence

ORD record: ord-abd12dfcd20d44bcbed71a6a4541e1bd
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06632826B1

Reaction notes

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