Ammonia → HCID 79848845, compound

Temperature

150 °C

Ethyl (2Z)-dihydrofuran-3(2H)-ylideneacetate (Preparation 36, 1.29 g, 8.25 mmol) was stirred in 1,4-dioxane (7 mL) in a microwave vial. A solution of 7M ammonia in methanol (5 mL) was added and the reaction heated for 4 hours at 150° C. in a Biotage Initiator™ microwave. The reaction was concentrated in vacuo, but later deemed not to have reached completion. A solution of 7M ammonia in methanol (7 mL) was added and the reaction heated again for 3 hours at 150° C. in the microwave. A further portion of 7M ammonia in methanol (3 mL) was added and the reaction heated for a further 2 hours. The reaction was concentrated in vacuo to afford the title compound along with the methyl ester where trans-esterification had occurred. The material was used without further purification in the next step.

1. concentrationThe reaction was concentrated in vacuo
2. additionA solution of 7M ammonia in methanol (7 mL) was added
3. temperaturethe reaction heated again for 3 hours at 150° C. in the microwave
4. additionA further portion of 7M ammonia in methanol (3 mL) was added
5. temperaturethe reaction heated for a further 2 hours
6. concentrationThe reaction was concentrated in vacuo

ORD record

ord-37f18b38cd504054b40ddee565b467b3

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09079878B2