Triethylamine → HCID 18329215, compound

HRID 1249964Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7](/[CH:12]=[CH:13]/[C:14]([O:16][CH3:17])=[O:15])[CH:6]=[CH:5]2.C(N(CC)CC)C.[C:25](Cl)(=[O:29])[C:26]([CH3:28])=[CH2:27]>C1COCC1>[CH3:28][C:26](=[CH2:27])[C:25]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7](/[CH:12]=[CH:13]/[C:14]([O:16][CH3:17])=[O:15])[CH:6]=[CH:5]2)=[O:29]

Participants

Conditions

Temperature: 0 °C

Procedure

0.89 g (3.9 mmol) of methyl (E)-3-(6-hydroxy-naphthalen-2-yl)-acrylate, a spatula tip of BHT and 0.66 ml of triethylamine were dissolved in 10 ml of THF. After cooling to 0° C. a solution of 0.39 ml (4.07 mmol) of methacryloyl chloride in 4 ml of THF was added dropwise within 30 minutes. The white suspension was stirred at 0° C. for a further hour and then partitioned in ether and water. The organic phase was back-washed twice with water and the aqueous phases were back-washed twice with diethyl ether. The combined organic phases were dried over magnesium sulphate, filtered over Celite and evaporated completely in a vacuum. The crude product was recrystallized from a mixture of 5 ml of hexane and 20 ml of toluene. This gave 0.92 g of white (E)-2-(2-methoxycarbonyl-vinyl)-naphthalen-6-yl 2-methyl-acrylate.

Workup

additionwas added dropwise within 30 minutes
custompartitioned in ether
washThe organic phase was back-washed twice with water
washthe aqueous phases were back-washed twice with diethyl ether
dry with materialThe combined organic phases were dried over magnesium sulphate
filtrationfiltered over Celite
customevaporated completely in a vacuum
customThe crude product was recrystallized from a mixture of 5 ml of hexane and 20 ml of toluene

Sources & evidence

ORD record: ord-6e5491ade6e54c7bbcaafc08461cecf8
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06335409B1

Reaction notes

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