Phosphoric Acid → HCID 15549881, compound

HRID 1082185Notes

Reaction equation

HRID 1082185 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].P(=O)(O)(O)O.C1(/C=[CH:16]/[C:17]([O:19][CH3:20])=O)CC1.S([O-])([O-])=[O:22].[Na+].[Na+].[C:27](O)([CH3:30])(C)[CH3:28].[OH2:32]>C1(C)C=CC=CC=1.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+].[Os](=O)(=O)(=O)=O>[CH:30]1([C@@H:1]([OH:4])[C@H:16]([OH:22])[C:17]([O:19][CH3:20])=[O:32])[CH2:27][CH2:28]1

Participants

9

Reactant 5

HCID 1004Phosphoric AcidHCID 11430Potassium CarbonateHCID 24437Sodium SulfiteHCID 1458555198272-33-4HCID 714019492-Methylpropan-2-ol--water (1/1)

Product 1

HCID 15549881HCID 15549881, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 178511488HCID 178511488, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 68.2 g of potassium ferricyanide and 28.6 g of potassium carbonate in 640 ml of tert-butanol-water (1:1) is added 0.537 g of 1,4-bis(9-O-dihydroquinidyl)phthalazine. The pH of the reaction mixture is adjusted to pH 10.9 with aqueous solution of phosphoric acid. After a solution of osmium tetroxide in 0.35 ml of toluene (0.393M) is added to the mixture, the resulting mixture is stirred at room temperature for 30 minutes. Then, methyl trans-3-cyclopropylacrylate is added to the mixture, and the mixture is stirred for 24 hours. After the reaction mixture is cooled with ice, 106 g of sodium sulfite is added to the mixture. Then, the mixture is stirred for 30 minutes. The mixture is extracted with ethyl acetate four times. The organic layer is dried and the solvent is removed in vacuo. The residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate=3:l) to give 4.22 g of methyl (2S,3R)-3-cyclopropyl--2,3-dihydroxypropionate.

Workup

  1. stirringthe mixture is stirred for 24 hours
  2. additionis added to the mixture
  3. stirringThen, the mixture is stirred for 30 minutes
  4. extractionThe mixture is extracted with ethyl acetate four times
  5. customThe organic layer is dried
  6. customthe solvent is removed in vacuo
  7. customThe residue is purified by silica gel column chromatography (solvent; hexane:ethyl acetate=3:l)

Sources & evidence

ORD record
ord-8f0a2e99035741889ac314e56035eb88
Source dataset
uspto-grants-1996_12
Patent number
US05589502

Reaction notes

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