Ethyl 2-(4-oxocyclohexyl)acetate → HCID 11095257, compound

HRID 1404409Notes

Reaction equation

HRID 1404409 reaction equation
[CH3:1][C:2]([O-])([CH3:4])[CH3:3].[K+].O=C1C[CH2:12][CH:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10]C1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:1]=[C:2]1[CH2:4][CH2:12][CH:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10][CH2:3]1

Participants

5

Reactant 2

HCID 12666966Ethyl 2-(4-oxocyclohexyl)acetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 11095257HCID 11095257, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (0° C.) suspension of methyl triphenylphosphonium bromide (8.58 g, 23.5 mmol) in THF (60 mL) was added KOtBu (3.17 g, 28.3 mmol) in portions under N2. The reaction was slowly warmed to rt and stirred for 1 h. The resulting mixture was cooled to 0° C. and added a solution of ethyl 2-(4-oxocyclohexyl)acetate (2.9 g, 15.7 mmol) in THF (15 mL). The resulting mixture was stirred at RT for 2 h and at 50° C. overnight. After cooling to RT, the reaction was quenched by addition of saturated NH4Cl, extracted with EtOAc, washed with brine, dried over Na2SO4. Purification by flash column chromatography (eluent: 20% EtOAc in hexanes) gave the product as colorless oil (2.11 g, 73.7%).

Workup

  1. temperatureTo a cooled
  2. temperatureThe resulting mixture was cooled to 0° C.
  3. stirringThe resulting mixture was stirred at RT for 2 h and at 50° C. overnight
  4. temperatureAfter cooling to RT
  5. customthe reaction was quenched by addition of saturated NH4Cl
  6. extractionextracted with EtOAc
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. customPurification by flash column chromatography (eluent: 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-43d45a5307d144d5bc4beaeb1cc4fb8a
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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