Diethyl Ether → HCID 13767771, compound

HRID 986330Notes

Reaction equation

HRID 986330 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[C:11]1\[C@:12]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])([O:17][Si](C)(C)C)[CH:13]=[CH:14][C:15]\1=[O:16])=[O:4].[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].CCOCC.[Cl-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[C:11]1\[C@@:12]([OH:17])([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:13]=[CH:14][C:15]\1=[O:16])=[O:4]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 5234Sodium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 13767767HCID 13767767, compound

Product 1

HCID 13767771HCID 13767771, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

113 mg (0.27 mmole) of (4R)-5-[(E)-6-methoxycarbonylhexylidene)-4-octyl-4-trimethylsilyloxy-2-cyclopentenone was dissolved in 20 ml of tetrahydrofuran, and at 0° C., 1 ml (1 mmole) of n-Bu4NF (1 M in THF) was added. The mixture was stirred for 15 minutes. Ether and a saturated aqueous solution of sodium chloride were added. The aqueous layer was extracted with ethyl acetate. After filtration and concentration, the residue was subjected to TLC (n-hexane:AcOEt=1:1) to obtain 31 mg (33%) of (4R)-5-[(E)-6-methoxycarbonylhexylidene)-4-hydroxy-4-octyl-2-cyclopentenone.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-ef1aa88e8e204b8993dcfe8aee7cdf10
Source dataset
uspto-grants-1987_12
Patent number
US04711895

Reaction notes

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