MAGNESIUM SILICATE (synthetic) → Betulone Aldehyde

HRID 414903Notes

Reaction equation

HRID 414903 reaction equation
[O-][Si]([O-])=O.[Mg+2].C([O-])(=O)C.[Na+].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:22][C:23]([C@H:25]1[C@@H:29]2[C@@H:30]3[C@@:43]([CH3:46])([CH2:44][CH2:45][C@@:28]2([CH2:52][OH:53])[CH2:27][CH2:26]1)[C@@:42]1([CH3:47])[C@@H:33]([C@:34]2([CH3:51])[C@@H:39]([CH2:40][CH2:41]1)[C:38]([CH3:49])([CH3:48])[C@@H:37]([OH:50])[CH2:36][CH2:35]2)[CH2:32][CH2:31]3)=[CH2:24]>C(Cl)Cl>[CH3:24][C:23]([C@H:25]1[C@@H:29]2[C@H:30]3[C@@:43]([CH3:46])([CH2:44][CH2:45][C@@:28]2([CH:52]=[O:53])[CH2:27][CH2:26]1)[C@:42]1([CH3:47])[CH2:41][CH2:40][C@H:39]2[C:38]([CH3:49])([CH3:48])[C:37](=[O:50])[CH:36]=[CH:35][C@:34]2([CH3:51])[C@H:33]1[CH2:32][CH2:31]3)=[CH2:22]

Participants

6

Reactant 4

HCID 61680MAGNESIUM SILICATE (synthetic)HCID 72326BetulinHCID 517045Sodium AcetateHCID 178418287HCID 178418287, compound

Product 1

HCID 44559212Betulone AldehydeYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of freshly activated powdered 4A molecular sieves (1.2 g), celite (1.2 g), florisil (1.2 g), sodium acetate (500 mg) and pyridinium chlorochromate (1.2 g) in CH2Cl2 (25 mL) add betulin (500 mg). The mixture is to be stirred for 2 hrs, and then filtered through a short column of silica gel. The filtrate is evaporated in vacuo. The residue is then subjected to column chromatography to afford betulone aldehyde (370 mg) as white solid.

Workup

  1. additionTo a suspension
  2. filtrationfiltered through a short column of silica gel
  3. customThe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-1845d7038c7d4ac7a5d33fed45637898
Source dataset
uspto-grants-2012_01
Patent number
US08088757B2

Reaction notes

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