Potassium Carbonate → Methyl (6S)-6,8-dihydroxyoctanoate

HRID 370323Notes

Reaction equation

HRID 370323 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N+](C1C=CC(C[O:15][C@H:16]([CH2:25][CH2:26][O:27]CC2C=CC([N+]([O-])=O)=CC=2)[CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=CC=1)([O-])=O>CO>[OH:15][C@H:16]([CH2:25][CH2:26][OH:27])[CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 20637815(6S)-(-)-methyl 6,8-bis(4-nitrobenzoxy)octanoate

Product 1

HCID 10899438Methyl (6S)-6,8-dihydroxyoctanoateYield 82.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under an argon atmosphere, anhydrous potassium carbonate (130 mg, 0.94 mmol) was added to a solution of (6S)-(-)-methyl 6,8-bis(4-nitrobenzoxy)octanoate (461 mg, 0.94 mmol) in methanol (9.4 ml). The mixture was stirred at room temperature for 1 h and quenched with a saturated ammonium chloride solution (50 ml). The mixture was extracted with chloroform (3×50 ml) and the combined organic extracts were washed with brine (50 ml). The organic phase was dried over magnesium sulphate and the solvent was evaporated under reduced pressure to give the crude product which was purified using flash column chromatography with ethyl acetate to give (6S)-(-)-methyl 6,8-dihydroxyoctanoate (147 mg, 82% yield) as a colourless oil. Rf 0.30 (ethyl acetate, 100%).

Workup

  1. customquenched with a saturated ammonium chloride solution (50 ml)
  2. extractionThe mixture was extracted with chloroform (3×50 ml)
  3. washthe combined organic extracts were washed with brine (50 ml)
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. customthe solvent was evaporated under reduced pressure
  6. customto give the crude product which
  7. customwas purified

Sources & evidence

ORD record
ord-e5216b6ee0b449ce80262def695c746f
Source dataset
uspto-grants-2000_10
Patent number
US06140512

Reaction notes

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