Acetic Acid → ALLYL 2-OXOCYCLOPENTANECARBOXYLATE

HRID 590689Notes

Reaction equation

HRID 590689 reaction equation
[C:1]([O:13][CH2:14][CH:15]=[CH2:16])(=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8]CC=C)=O.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C(O)(=O)C>O1CCCC1>[O:8]=[C:6]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:1]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 18139Hexanedioic acid, 1,6-di-2-propen-1-yl esterHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 11008303ALLYL 2-OXOCYCLOPENTANECARBOXYLATEYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of diallyl adipate (4.53 g, 20 mmol) in anhydrous tetrahydrofuran (100 mL) was cooled to 0° C. and treated with lithium bis(trimethylsilyl)amide (40 mL, 1.0 N in THF, 40 mmol). After the addition was complete, the solution was warmed to room temperature and stirred for 2 h. The solution was then recooled to 0° C. and treated with acetic acid (2.53 mL, 44 mmol) in a dropwise manner. The turbid mixture was warmed to room temperature and filtered. The filtrate was concentrated, dissolved in minimal dichloromethane and purified by flash column chromatography (silica gel, dichloromethane) to afford allyl 2-oxocyclopentanecarboxylate (2.62 g, 78%) as a colorless oil. Characterization data is same as that observed from method A.

Workup

  1. additionAfter the addition
  2. customwas then recooled to 0° C.
  3. temperatureThe turbid mixture was warmed to room temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. dissolutiondissolved in minimal dichloromethane
  7. custompurified by flash column chromatography (silica gel, dichloromethane)

Sources & evidence

ORD record
ord-a1f125320c5f4e62955675636c91ecef
Source dataset
uspto-grants-2016_01
Patent number
US09233985B2

Reaction notes

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