Potassium Hydroxide → HCID 58487982, compound

HRID 888182Notes

Reaction equation

HRID 888182 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([C:20]([O:22]C(C)C)=[O:21])[C@@H:12]([OH:19])[C:13]([O:15]C(C)C)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C1COCC1.O>[C:20]([C@@H:11]([CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@@H:12]([OH:19])[C:13]([OH:15])=[O:14])([OH:22])=[O:21]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 58487993HCID 58487993, compound

Product 1

HCID 58487982HCID 58487982, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

isopropyl 5-O-benzyl-3,4-dideoxy-3-(isopropoxycarbonyl)-L-threo-pentonate (7 g, 19.8 mmol) was taken in THF (50 mL), cooled to 0° C. and was treated with KOH (5.5 g, 99 mmol) in water (50 mL). The resulting mixture was stirred at RT for 3 h. THF was removed and the residue was taken in water. The aqueous layer was washed with ether (100 mL) and was acidified with an aqueous solution of HCl (1.5 N), then was then further extracted with EtOAc (2×100 mL), washed with water, dried over Na2SO4 and then concentrated to give the title product as colorless liquid (3.5 g).

Workup

  1. customTHF was removed
  2. washThe aqueous layer was washed with ether (100 mL)
  3. extractionwas then further extracted with EtOAc (2×100 mL)
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-03756c187c5c4f8e9c0b7193066593d1
Source dataset
uspto-grants-2012_08
Patent number
US08247437B2

Reaction notes

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