Potassium Fluoride → HCID 58456286, compound

HRID 1039986Notes

Reaction equation

HRID 1039986 reaction equation
C[Si](C)(C)[O:3][C:4]1[CH2:11][C:8]2([CH2:10][CH2:9]2)[CH:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:6][CH:5]=1.[F-].[K+]>CO>[O:3]=[C:4]1[CH2:11][C:8]2([CH2:9][CH2:10]2)[CH:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 67249603Ethyl 7-[(trimethylsilyl)oxy]spiro[2.5]oct-6-ene-4-carboxylate

Product 1

HCID 58456286HCID 58456286, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of Step 1 (1.698 g, 6.33 mmol) was dissolved in methanol (6 ml). Potassium fluoride (0.404 g, 6.96 mmol) was added, and the solution was maintained at room temperature for 1 hour. The solution was concentrated in vacuo. Purification via silica gel column chromatography (0-25% EtOAc:Hexanes) afforded ethyl 7-oxospiro[2.5]octane-4-carboxylate (251 mg, 20%) as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 4.27-4.14 (m, 2H), 2.90 (d, J=14.9, 1H), 2.66 (ddd, J=5.6, 11.4, 16.8, 1H), 2.42-2.25 (m, 2H), 2.15-2.04 (m, 2H), 1.68 (d, J=14.9, 1H), 1.34-1.26 (m, 3H), 0.76-0.67 (m, 1H), 0.50-0.40 (m, 2H), 0.40-0.31 (m, 1H).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customPurification via silica gel column chromatography (0-25% EtOAc:Hexanes)

Sources & evidence

ORD record
ord-9f261e7691cf4048aca569893baf7cbe
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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