Sodium periodate → HCID 69058233, compound

HRID 1727229Notes

Reaction equation

HRID 1727229 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:14]2[O:15][C:16]([CH3:19])([CH3:18])[O:17][C@:13]32[C@H:8]([C@H:9]([C:21]([OH:25])(C)[CH2:22]O)[CH2:10][CH2:11][C@@H:12]3[CH3:20])[CH:7]=[C:6]1[CH3:26])(=[O:3])[CH3:2].I([O-])(=O)(=O)=O.[Na+]>CO.O>[C:1]([O:4][C@H:5]1[C@@H:14]2[O:15][C:16]([CH3:18])([CH3:19])[O:17][C@:13]32[C@H:8]([C@H:9]([C:21](=[O:25])[CH3:22])[CH2:10][CH2:11][C@@H:12]3[CH3:20])[CH:7]=[C:6]1[CH3:26])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 23667635Sodium periodate3×HCID 69056271HCID 69056271, compound

Product 1

HCID 69058233HCID 69058233, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of the product of (3aS,4R,6aS,7R,10S,10aS)-7-(1,2-dihydroxy-1-methylethyl)-2,2,5,10-tetramethyl-4,6a,7,8,9,10-hexahydro-3aH-naphtho[1,8a-d][1,3]dioxol-4-yl acetate (Preparation 147, 930 mg) in methanol (50 ml) was treated with sodium periodate (540 mg) and sonicated in an ultrasonic bath for 15 minutes. As the sodium periodate dissolved, a cloudy suspension formed. A further amount of sodium periodate (540 mg) was added and sonication was resumed for 15 min. After standing for 1 hour, the reaction mixture was diluted with water and solvent was evaporated. The residue was partitioned between water and dichloromethane and the organic phase was separated, washed with water and brine, dried (Na2SO4) and, concentrated in vacuo. The residual oil was purified by flash column chromatography on silica gel eluting with ethyl acetate:hexane (1:4) to give the product as a colourless oil (680 mg).

Workup

  1. customsonicated in an ultrasonic bath for 15 minutes
  2. customa cloudy suspension formed
  3. customsonication
  4. waitAfter standing for 1 hour
  5. customwas evaporated
  6. customThe residue was partitioned between water and dichloromethane
  7. customthe organic phase was separated
  8. washwashed with water and brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated in vacuo
  11. customThe residual oil was purified by flash column chromatography on silica gel eluting with ethyl acetate:hexane (1:4)

Sources & evidence

ORD record
ord-87c3710da78644a7999bb07be7aad3c5
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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