Citric Acid → (1RS,4RS)-3-allyl-4-methyl-4-hydroxy-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether

HRID 582739Notes

Reaction equation

HRID 582739 reaction equation
[Si:1]([O:8][CH:9]1[CH2:13][C:12](=[O:14])[C:11]([CH2:15][CH:16]=[CH2:17])=[CH:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O1CCC[CH2:19]1.C[Li].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(OCC)C>[Si:1]([O:8][CH:9]1[CH2:13][C:12]([CH3:19])([OH:14])[C:11]([CH2:15][CH:16]=[CH2:17])=[CH:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 14189022(RS)-3-allyl-4-oxo-2-cyclopenten-1-yl (t-butyldimethylsilyl) etherHCID 178418348HCID 178418348, compound

Product 1

HCID 57153596(1RS,4RS)-3-allyl-4-methyl-4-hydroxy-2-cyclopenten-1-yl (t-butyldimethylsilyl) etherYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution mixture of 5 g of (RS)-3-allyl-4-oxo-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether and 50 ml of tetrahydrofuran was added under nitrogen stream 23.7 ml of 1.07 M diethyl ether solution of methyllithium at -78° C. and the resulting mixture was stirred at the same temperature for 2 hours. Then, the reaction liquid was poured into ice-cooled 5% aqueous solution of citric acid and extracted two times with diethyl ether. The combined ether layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 4.7 g of (1RS,4RS)-3-allyl-4-methyl-4-hydroxy-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether. Yield 84%

Workup

  1. additionwas added under nitrogen
  2. customat -78° C.
  3. customThen, the reaction liquid
  4. additionwas poured into ice-
  5. extractionextracted two times with diethyl ether
  6. washThe combined ether layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue thus obtained

Sources & evidence

ORD record
ord-8f2e139620554ad5b75d331127cfb2dc
Source dataset
uspto-grants-1999_07
Patent number
US05925676

Reaction notes

Loading…