Tetrahydrofuran → 2-Phenyl-2-methyl-4-pentenoyl cyclohexane

HRID 2306642Notes

Reaction equation

HRID 2306642 reaction equation
[CH3:1][C:2]([O-])(C)[CH3:3].[K+].[C:7]1([CH:13]([C:15]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=O)[CH3:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1C[O:26]CC1>>[C:7]1([C:13]2([CH3:14])[CH2:15][CH:17]([C:22](=[O:26])[CH:21]=[CH:20][CH2:19][CH3:18])[CH2:3][CH2:2][CH2:1]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran3×HCID 142241151-Cyclohexyl-2-phenylpropan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 694234192-Phenyl-2-methyl-4-pentenoyl cyclohexaneYield 91.58%

Procedure

A solution of 31.39 g (0.2797 mol) of t-BuOK in 100 mL of THF was added dropwise to a solution of 55.00 g (0.2543 mol) of cyclohexyl 1-phenylethyl ketone and 26.4 mL (0.3052 mol) of alkyl bromide in 136 mL of THF (cooled in a wet ice acetone bath). THF washings (16 mL) were added to the reaction mixture. The cooling bath was removed after addition. After reaction completion (2 h), the reaction mixture was quenched with 300 mL of 1 N HCl (pH=0) and extracted with 300 mL of heptane. The heptane extract was washed with 10% NaHCO3 (aq) (pH=9), dried over MgSO4, gravity filtered and concentrated under vacuum to afford 59.70 g (91.58%) of title compound as an amber oil: 1H NMR (d6-DMSO): δ 7.32-7.42 (m, 2H, phenyl CH), 7.24-7.31 (m, 3H, phenyl CH), 5.34-5.47 (m, 1H, —CH═CH2), 5.02 (dd, J=17.1 Hz, J=2.1 Hz, 1H, —CH═CH—H (trans)), 4.97 (ddd, J=10.2 Hz, J=2.2 Hz, J=1.0 Hz, 1H, —CH═CH—H (cis, W-coupling)), 2.66 (ddd, J=14.2 Hz, J=6.9 Hz, J=1.0 Hz, 1H, —CH2CH═CH2), 2.59 (ddd, J=14.2 Hz, J=7.3 Hz, J=1.0 Hz, 1H, —CH2CH═CH2), 2.38-2.49 (m, 1H, cyclohexyl CH), 1.48-1.69 (m, 4H, cyclohexyl-CH2), 1.46 (s, 3H, —CH(CH3)Ph), 1.36-1.44 (m, 1H, cyclohexyl-CH2), 0.82-1.36 (m, 5H, cyclohexyl-CH2).

Workup

  1. customThe cooling bath was removed
  2. additionafter addition
  3. customAfter reaction completion (2 h)
  4. customthe reaction mixture was quenched with 300 mL of 1 N HCl (pH=0)
  5. extractionextracted with 300 mL of heptane
  6. extractionThe heptane extract
  7. washwas washed with 10% NaHCO3 (aq) (pH=9)
  8. dry with materialdried over MgSO4, gravity
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0c3d04bcbbf743969496605e56118861
Source dataset
uspto-grants-2004_12
Patent number
US06828332B1

Reaction notes

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