Diethyl Ether → 3-Cyclohexyl-1-cyclopentyl-propan-1-one

HRID 1453026Notes

Reaction equation

HRID 1453026 reaction equation
N1C=CC=CC=1S[C:8](=[O:17])[CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[CH:18]1([Mg]Br)[CH2:22][CH2:21][CH2:20][CH2:19]1.CCOCC>C1COCC1>[CH:11]1([CH2:10][CH2:9][C:8]([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 587624843-Cyclohexyl-thiopropionic Acid S-pyridin-2-yl EsterHCID 178419650HCID 178419650, compound

Product 1

HCID 587625123-Cyclohexyl-1-cyclopentyl-propan-1-oneYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

3-Cyclohexyl-thiopropionic acid S-pyridin-2-yl ester (1.43 g, 5.74 mmol) from Step 1 above was dissolved in dry THF (28 mL) and cooled to −78° C. A solution of cyclopentylmagnesium bromide in Et2O (2.0 M, 3.01 mL, 6.02 mmol) was added dropwise. After stirring 1 h, the cooling bath was removed. The reaction mixture was quenched with 1N HCl and extracted with EtOAc (100 mL). The organic phase was washed with brine (50 mL), dried over Na2SO4 and evaporated. The residue was purified by flash column chromatography (1% EtOAc in hexanes) to give the product (0.99 g, 83%) as clear oil. 1H NMR (CDCl3) δ: 0.82-1.84 (m, 21H), 2.42-2.47 (m, 2H), 2.82-2.92 (m, 1H).

Workup

  1. customthe cooling bath was removed
  2. customThe reaction mixture was quenched with 1N HCl
  3. extractionextracted with EtOAc (100 mL)
  4. washThe organic phase was washed with brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by flash column chromatography (1% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2e6511cb44394d8c9557e48253159e98
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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