Isopropanol → HCID 54545639, compound

HRID 483654Notes

Reaction equation

[F:1][C:2]([CH:9]=[CH:10][CH:11]([F:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:3][CH:4]=[CH:5][CH:6]=[CH:7][OH:8].CC(C)=[O:26].OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O>[F:1][C:2](=[CH:9][CH:10]=[C:11]([F:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:3]=[CH:4][CH:5]=[CH:6][C:7]([OH:26])=[O:8]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the alcohol prepared in 3P (282 mg, 0.86 mmoles) in acetone (7 ml) cooled to 0° C. was added dropwise 2.67M Jones reagent over 15 min. until the orange 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 up 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. Flash chromatography on silica gel and elution with a 15:85 mixture of ethyl acetate and benzene gave pure acid (180 mg, 61%).

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
customto leave an oil
washFlash chromatography on silica gel and elution
additionwith a 15:85 mixture of ethyl acetate and benzene

Sources & evidence

ORD record: ord-f9fd1b962e2341639605949a4dc2a2cc
Source dataset: uspto-grants-1993_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05225429

Reaction notes

Loading…