Tetrahydrofuran → 2-Phenethyl-cyclohexanone

HRID 271840

Reaction equation

HRID 271840 reaction equation
[Li][CH:2](CC)[CH3:3].Cl[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:15]1[CH2:19][O:18][CH2:17][CH2:16]1>>[CH2:7]([CH:15]1[CH2:16][CH2:17][CH2:3][CH2:2][C:19]1=[O:18])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2314961-Chloro-2-phenylethaneHCID 178418400CID 53628100

Product 1

HCID 2316152-Phenethyl-cyclohexanone

Conditions

Temperature
-78 °C

Procedure

s-BuLi (28.0 mL, 1.3 M) was added slowly to a solution of Compound 20b (7.0 g) in THF (50 mL) at −78° C. The mixture stirred for 1 hr at −78° C. and then (2-chloro-ethyl)-benzene Compound 20c (5.11 g, 36.4 mmol) in THF (10 mL) was added dropwise. The reaction mixture was stirred for 24 hrs while warming to r.t. The reaction was quenched with 1N HCl (5 mL), then diluted with water (100 mL) and EtOAc (500 mL). The organic layer was washed with brine, separated and dried with anhydrous sodium sulfate, then filtered and concentrated in vacuo to yield a crude product. Purification by flash chromatography (eluted with 10% EtOAc in Hexane) afforded 2-phenethyl-cyclohexanone Compound 20d (4.05 g, 20.0 mMol, 58%) as a yellow oil.

Workup

  1. stirringThe reaction mixture was stirred for 24 hrs
  2. temperaturewhile warming to r.t
  3. customThe reaction was quenched with 1N HCl (5 mL)
  4. additiondiluted with water (100 mL) and EtOAc (500 mL)
  5. washThe organic layer was washed with brine
  6. customseparated
  7. dry with materialdried with anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto yield a crude product
  11. customPurification
  12. washby flash chromatography (eluted with 10% EtOAc in Hexane)

Sources & evidence

ORD record
ord-5e24323ad1164353bd8e9c877b49b9ce
Source dataset
uspto-grants-2008_11
Patent number
US07452997B2

Linked notes

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