Diethyl Ether → HCID 20158400, compound

HRID 986333Notes

Reaction equation

HRID 986333 reaction equation
[Si](O[C:9]1[C:13](=[O:14])[CH2:12][C:11]([OH:26])([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:10]=1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].O.O.O.[Cl-].[Na+].CCOCC>O1CCCC1>[O:19]([CH2:18][CH2:17][CH2:16][CH2:15][C:11]1([OH:26])[CH2:12][CH:13]([OH:14])[CH:9]=[CH:10]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 5234Sodium ChlorideHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 23182903HCID 23182903, compound

Product 1

HCID 20158400HCID 20158400, compoundYield 677.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8 g (22 mmoles) of 5-t-butyldimethylsilyloxy-3-hydroxy-3-(4-phenoxybutyl)cyclopentenone was dissolved in 25 ml of tetrahydrofuran, and 11 g (35 mmoles) of n-Bu4NF.3H2O was added. The mixture was stirred at room temperature for 4 hours. After the addition, a saturated sodium chloride solution and ether were added. The aqueous layer was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate. After filtration and concentration, the residue was chromatographed on a silica gel column (hexane:AcOEt=1:2) to give 37 g (68%) of 4-(4-phenoxybutyl)cyclopent-2-ene-1,4-diol.

Workup

  1. additionAfter the addition
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationAfter filtration and concentration
  5. customthe residue was chromatographed on a silica gel column (hexane:AcOEt=1:2)

Sources & evidence

ORD record
ord-e6eab5793e5949a79483f988e7f576ee
Source dataset
uspto-grants-1987_12
Patent number
US04711895

Reaction notes

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