Isopropanol → HCID 90388634, compound

HRID 2201741Notes

Reaction equation

HRID 2201741 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[OH:14][C@H:15]1[C@:19]2([CH3:33])[CH2:20][C@H:21]3[C@H:30]([CH2:31][C@H:18]2[CH2:17][CH2:16]1)[C@@H:29]1[C@H:24]([CH2:25][C:26](=[O:32])[CH2:27][CH2:28]1)[CH2:23][CH2:22]3.CC(O)C>CC(C)=O>[CH3:33][C@:19]12[C:15](=[O:14])[CH2:16][CH2:17][C@@H:18]1[CH2:31][C@H:30]1[C@@H:21]([CH2:22][CH2:23][C@@H:24]3[C@@H:29]1[CH2:28][CH2:27][C:26](=[O:32])[CH2:25]3)[CH2:20]2

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 90388608HCID 90388608, compoundHCID 131709961Jones' reagent

Product 1

HCID 90388634HCID 90388634, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones reagent was added to a solution of compound 37 (605 mg, 2.2 mmol) in acetone (40 mL) at 0° C. until a brown-yellowish color persisted. After 10 min, 2-propanol (1.0 mL) was added to consume excess oxidant. Brine (50 mL) was added and the product 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 38 (580 mg, 96%) as a white solid: [α]D25 −13.1 (c 0.145, CHCl3); 1H NMR (CDCl3) δ 0.81 (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, 3.54, 34.0, 33.4, 29.9, 28.7, 23.8, 13.4; IR νmax 1716, 1715 cm−1.

Workup

  1. customto consume excess oxidant
  2. additionBrine (50 mL) was added
  3. extractionthe product extracted into EtOAc (50 mL×3)
  4. customThe combined extracts were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (silica gel eluted with 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ae1d822120254494ae8698d90a993324
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

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