Water → HCID 13924083, compound

Temperature

70 °C

3-(4-Hydroxybut-1-yl)cyclopentene {2-cyclopentene-1-butanol}(51 g, 0.37 moles) is diluted in dimethylformamide (100 ml) and added to pyridine (38 g, 0.40 moles). The solution is stirred and methane sulfonyl chloride (46 g, 0.40 moles) is added dropwise in the course of 10 minutes. The reaction is then heated in a 70° C. water bath for 30 minutes. Then the mixture is cooled and water (1 liter) is added over 20 minutes. The reaction is partitioned between hexane (500 ml) and the organic phase separated. The aqueous layer is extracted with hexane (2×500 ml) and the extracts combined with the organic layer. The solvent volume is reduced under vacuum and the residue dried over anhydrous magnesium sulfate. The solid is filtered off and the remaining solvent removed leaving a clear yellow oil. The crude product is fractionally distilled under reduced presure leaving a clear, colorless oil (43 g, 0.27 moles), BP 40° C./0.2 mm.

1. temperatureThen the mixture is cooled
2. customThe reaction is partitioned between hexane (500 ml)
3. customthe organic phase separated
4. extractionThe aqueous layer is extracted with hexane (2×500 ml)
5. dry with materialthe residue dried over anhydrous magnesium sulfate
6. filtrationThe solid is filtered off
7. customthe remaining solvent removed
8. customleaving a clear yellow oil
9. distillationThe crude product is fractionally distilled under reduced presure

ORD record

ord-0471832c8b414493b0ecb67e377b1ac4

Source dataset

uspto-grants-1987_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04689345