Potassium Sodium Tartrate → HCID 13062052, compound

HRID 2166541Notes

Reaction equation

HRID 2166541 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@:9]23[CH2:21][CH2:20][CH2:19][CH2:18][C@@H:10]2[N:11]([CH3:17])[C:12](=O)[C@@H:13]([CH3:15])[O:14]3)[CH:6]=[CH:7][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@:9]23[CH2:21][CH2:20][CH2:19][CH2:18][C@@H:10]2[N:11]([CH3:17])[CH2:12][C@@H:13]([CH3:15])[O:14]3)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 13062049HCID 13062049, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13062052HCID 13062052, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The crude product of Example 10 (1.36 g) in dry ether (25 cm3) was added dropwise to a stirred, refluxing suspension of lithium aluminium hydride (0.45 g) in dry ether (10 cm3). The mixture was heated to reflux for 6 hr. and was then allowed to cool. Saturated Rochelle salt solution (50 cm3) was added and the mixture was stirred to dissolve aluminium salts. The phases were separated and the aqueous phase was extracted with further ether. The extracts were dried (Na2SO4) and evaporated, leaving the title product as an oil (1.27 g). The crude title base (1.1 g) was converted in ethyl acetate to its hydrogen oxalate salt, which was recrystallised from ethyl acetate-methanol giving crystals (0.73 g), m.p. 213°-5° (decomp.).

Workup

  1. temperaturerefluxing
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 6 hr
  4. temperatureto cool
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted with further ether
  7. dry with materialThe extracts were dried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-6ee4052eb23e4c9a95b01ffdffbe2e17
Source dataset
uspto-grants-1983_06
Patent number
US04387097

Reaction notes

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