Tetrahydrofuran → HCID 23081548, compound

4-Fluorobenzyl alcohol (3.00 g, 23.8 mmol) was dissolved in THF (60 ml), to which 1,1′-carbonyldiimidazole (4.05 g, 25.0 mmol) was added while cooling in an ice-bath, and the mixture was stirred for 30 minutes. 2-Methallylamine hydrochloride (2.81 g, 26.2 mmol) and triethylamine (3.98 g, 28.5 mmol) were added to the mixture, which was stirred for 2 hours. After the reaction mixture was concentrated under reduced pressure, water were added to the residue, and the mixture was extracted with methylene chloride twice. The extracts were combined, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1) to afford 4-fluorobenzyl N-(2-methyl-2-propenyl)carbamate (4.69 g, yield 88%) as a colorless oil.

1. additionwas added
2. temperaturewhile cooling in an ice-bath
3. stirringwas stirred for 2 hours
4. concentrationAfter the reaction mixture was concentrated under reduced pressure, water
5. additionwere added to the residue
6. extractionthe mixture was extracted with methylene chloride twice
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under reduced pressure
10. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1)

ORD record

ord-0f42c94adff24ad7b3c42f8069052da4

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07262212B2