Isopropanol → HCID 54083316, compound

HRID 1885642Notes

Reaction equation

[F:1][C:2]([CH2:9][CH:10]=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].CC(C)=[O:25].OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O>[F:1][C:2]([CH2:9][CH:10]=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:3][CH2:4][CH2:5][CH2:6][C:7]([OH:25])=[O:8]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the alcohol prepared in 2K (21 mg, 0.067 mmoles) in acetone (2 ml) cooled to 0° C. was added dropwise 2.67M Jones reagent until the organe color was stable. The mixture was stirred 15 min at 0° C. The excess of Jones reagent was reacted with isopropanol. The acetone was evaporated under reduced pressure without heating. The residue was taken with water and extracted three times with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to leave an oil (20 mg). Flash chromatography on silicagel and elution with a 25:75 mixture of ethyl acetate and hexane gave pure title acid (14 mg, 64%). NMR (H1, CDCl3, 360 MHz): 0.89 (t, JHH ~7 Hz, 3), 1.21 to 1.45 (m, 10), 1.51 (quint, JHH ~7 Hz, 2), 1.98 to 2.12 (m, 8), 2.37 (t, JHH ~7 Hz, 2), 2.96 (dd, JHF =23 Hz, JHH =6.8 Hz, 2), 4.98 (dt, JHH =21.2Hz, JHH =7.9 Hz, ]), 5.3 to 5.5 (m, 4).

Workup

customThe acetone was evaporated under reduced pressure
temperaturewithout heating
extractionextracted three times with ethyl acetate
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-28f47595bb04477a9c0f174f2744fb11
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05145861

Reaction notes

Loading…