Isopropanol → HCID 90388246, compound

HRID 2201733Notes

Reaction equation

HRID 2201733 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[CH3:14][C@@:15]12[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][C@H:24]1[CH2:23][CH2:22][C@H:21]1[C@H:16]2[CH2:17][C@@H:18]2[CH2:32][CH2:31][C@H:30]([OH:33])[C@@:19]2([CH3:34])[CH2:20]1.CC(O)C>CC(C)=O.[Cl-].[Na+].O>[CH3:34][C@@:19]12[C:30](=[O:33])[CH2:31][CH2:32][C@H:18]1[CH2:17][C@@H:16]1[C@H:21]([CH2:22][CH2:23][C@H:24]3[C@@:15]1([CH3:14])[CH2:28][CH2:27][C:26](=[O:29])[CH2:25]3)[CH2:20]2

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 90387811HCID 90387811, compoundHCID 131709961Jones' reagent

Product 1

HCID 90388246HCID 90388246, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Jones reagent was added to a solution of compound 20 (480 mg, 1.66 mmol) in acetone (40 mL) at 0° C. until a brown-yellowish color persisted. After 10 min, 2-propanol (1.0 mL) was added and then brine (50 mL) was added. The product was extracted into EtOAc (50 mL×3). The combined extracts were dried, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel eluted with 20% EtOAc in hexanes) to give compound 21 (461 mg, 96%): 1H NMR (CDCl3) δ 1.02 (s, 3H), 0.87 (s, 3H); 13C NMR (CDCl3) δ 220.1, 211.0, 48.2, 47.8, 47.6, 45.6, 45.4, 43.5, 40.9, 38.9, 37.6, 35.4, 34.0, 33.4, 29.9, 28.7, 23.8, 13.4; IR νmax 1734, 1714 cm−1.

Workup

  1. extractionThe product was extracted into EtOAc (50 mL×3)
  2. customThe combined extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (silica gel eluted with 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3e68f0dfeedb4bef9131140598dcf059
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

Loading…