Potassium chromate(VI) → HCID 59557758, compound

HRID 2174338Notes

Reaction equation

HRID 2174338 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][CH3:34])=[CH:29][CH:28]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:35][O:36][C:37](=[O:39])[CH3:38])(=[O:3])[CH3:2].[Cr]([O-])([O-])(=O)=[O:41].[K+].[K+]>C(O)(=O)C>[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([C:33](=[O:41])[CH3:34])=[CH:31][CH:32]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:35][O:36][C:37](=[O:39])[CH3:38])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24597Potassium chromate(VI)HCID 11671302HCID 11671302, compound

Product 1

HCID 59557758HCID 59557758, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-ethylbenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (10 g, 10.8 mmol) in acetic acid (130 mL) at 120° C. was added potassium chromate (6.3 g, 21.4 mmol) in one portion. The mixture was stirred for 22 hours at this temperature, and the reaction was cooled to RT. The volatiles were removed under reduced pressure, ethyl acetate was added, and the solids were filtered off. The organic layer was washed with a saturated solution of sodium bicarbonate and then with brine, and dried over sodium sulfate. Concentration of the organic solution and purification of the resulting residue by silica gel column (3:1 petroleum ether:ethyl acetate) gave 2.3 g of title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.90 (d, J=8.0 Hz, 2H), 7.39 (d, J=8.4 Hz, 1H), 7.26 (d, J=8.4 Hz, 2H), 7.22 (dd, J=8.4, 2.2 Hz, 1H), 7.17 (d, J=2.0 Hz, 1H), 5.31 (t, J=9.4 Hz, 1H), 5.22 (t, J=9.8 Hz, 1H), 5.09 (t, J=9.4 Hz, 1H), 4.35 (d, J=10.0 Hz, 1H), 4.29 (dd, J=12.4, 4.8 Hz, 1H), 4.18-4.13 (m, 3H), 3.85-3.81 (m, 1H), 2.60 (s, 3H), 2.09 (s, 3H), 2.07 (s, 3H), 2.01 (s, 3H), 1.75 (s, 3H); MS ESI (m/z): 575 [M+H]+, 619 [M+HCO2]−.

Workup

  1. customThe volatiles were removed under reduced pressure, ethyl acetate
  2. additionwas added
  3. filtrationthe solids were filtered off
  4. washThe organic layer was washed with a saturated solution of sodium bicarbonate
  5. dry with materialwith brine, and dried over sodium sulfate
  6. customConcentration of the organic solution and purification of the resulting residue by silica gel column (3:1 petroleum ether:ethyl acetate)

Sources & evidence

ORD record
ord-11713050daff42b9acf4c98c91ebf03c
Source dataset
uspto-grants-2015_06
Patent number
US09061060B2

Reaction notes

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