Isopropanol → HCID 86745099, compound

HRID 728889Notes

Reaction equation

HRID 728889 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([CH:11]=[C:12]([CH3:26])[CH2:13][CH2:14][CH2:15][P:16]([O:22][CH:23]([CH3:25])[CH3:24])([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].C([OH:31])(C)C.C(OCC)(=O)C.[Cl-].[Na+]>[O-2].[O-2].[O-2].[Cr+6].S(=O)(=O)(O)O.CC(C)=O>[C:1]([O:5][C:6]([NH:7][C@H:8]([CH:11]=[C:12]([CH3:26])[CH2:13][CH2:14][CH2:15][P:16]([O:18][CH:19]([CH3:20])[CH3:21])([O:22][CH:23]([CH3:25])[CH3:24])=[O:17])[C:9]([OH:31])=[O:10])=[O:27])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 3776IsopropanolHCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 57077108HCID 57077108, compound

Product 1

HCID 86745099HCID 86745099, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 1118Sulfuric AcidSolventHCID 10219390chromium (VI) trioxideSolvent

Procedure

0.84 ml of a solution which is 3.25 molar in chromium trioxide and 5.29 molar in sulphuric acid is added dropwise at 0°-5° to a solution of 0.5 g of alcohol 8 according to h) in 15 ml of acetone. The mixture is stirred at 0° for 30 minutes and at room temperature for35 minutes, and then 4 ml of isopropanol, 80 ml of ethyl acetate and 30 ml of 20% sodium chloride solution are added thereto, and the mixture is filtered. The aqueous phase is extracted three times with 20 ml of ethyl acetate each time. The organic phase is dried over sodium sulphate and concentrated by evaporation. Chromatography on 20 g of silica gel using hexane/ethyl acetate/acetic acid 16:10:1 yields 0.34 g of 9, [α]D =-35.25° (c=1.39, CHCl3), --C-NMR (75 MHz, CDCl3): 173.8 (CO2H); 155.0 (OCON); 140.4 (C(4)); 121.1 (C(3)); 79.5 (OC(CH3)3); 70.3 (OCH); 52.1 (C(2)); 39.7 (d, J=18, C(5)); 28.3 ((CH3)3C); 25.7 (d, J=142, C(7)); 24.0 ((CH3)2CH); 20.2 (d, J=5, C(6)).

Workup

  1. filtrationthe mixture is filtered
  2. extractionThe aqueous phase is extracted three times with 20 ml of ethyl acetate each time
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-b745fe92b39640848468646ffbce579d
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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