Tosylmethyl isocyanide → HCID 178442249、化合物

PCC (15.4 g, 71.4 mmol) was added to an ambient temperature solution of 3-methyl-3-(trifluoromethyl)pent-4-en-1-ol (4.0 g, 23.8 mmol) in methylene chloride (100 mL). After stirring at ambient temperature for 1.5 h, celite was added and the reaction stirred vigorously for 10 min. The reaction mixture was filtered through celite and concentrated in vacuo. TOSMIC (9.3 g, 47.6 mmol) followed by potassium tert-butoxide (cat.) were added to a solution of crude residue in tetrahydrofuran (50 mL). After stirring at ambient temperature for 2 h, the reaction mixture was concentrated in vacuo. Ammonia (7 N in methanol) (50 mL) was added to the crude residue. After stirring at 100° C. overnight, the reaction mixture was cooled and concentrated in vacuo. The residue was partitioned between 10% aqueous sodium hydroxide and methylene chloride. The aqueous phase was extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% acetone/methylene chloride afforded 4-[2-methyl-2-(trifluoromethyl)but-3-en-1-yl]-1H-imidazole.

1. additioncelite was added
2. stirringthe reaction stirred vigorously for 10 min
3. filtrationThe reaction mixture was filtered through celite and
4. concentrationconcentrated in vacuo
5. stirringAfter stirring at ambient temperature for 2 h
6. concentrationthe reaction mixture was concentrated in vacuo
7. additionAmmonia (7 N in methanol) (50 mL) was added to the crude residue
8. stirringAfter stirring at 100° C. overnight
9. temperaturethe reaction mixture was cooled
10. concentrationconcentrated in vacuo
11. customThe residue was partitioned between 10% aqueous sodium hydroxide and methylene chloride
12. extractionThe aqueous phase was extracted with methylene chloride
13. dry with materialThe combined organic extracts were dried (magnesium sulfate)
14. concentrationconcentrated in vacuo

ORDレコード

ord-a087dc678f0043b4ae124a8429336180

出典データセット

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08106070B2