Hydrochloric Acid → 3-Phenoxy-6-(3-phenyl-acryloyl)cyclohex-2-enone

HRID 1861065Notes

Reaction equation

HRID 1861065 reaction equation
[O:1]([C:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:25](Cl)(=[O:34])[CH:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl>C1COCC1>[O:1]([C:8]1[CH2:13][CH2:12][CH:11]([C:25](=[O:34])[CH:26]=[CH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:10](=[O:14])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 660233-Phenylprop-2-enoyl chlorideHCID 2733832Lithium HexamethyldisilazideHCID 36542163-Phenoxy-cyclohex-2-enone

Product 1

HCID 693717203-Phenoxy-6-(3-phenyl-acryloyl)cyclohex-2-enoneYield 43.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-phenoxy-cyclohex-2-enone (301 mg, 1.6 mmol) in 1 mL of THF was added to a stirred solution of 1.0 M solution of lithium bis(trimethylsilyl)amide in THF (3.2 mL) at −78° C. After 15 min, cinnamoyl chloride (266 mg, 1.6 mmol) was added all at once. After 15 min, the reaction mixture was poured into 0.5 N HCl and extracted with EtOAc (2×). The combined organic layers were washed with saturated NaCl solution, dried (MgSO4), filtered, and concentrated under reduced pressure. Chromatography of the residue with 4:1 hexanes/ethyl acetate as eluant provided 220 mg (43%) of 3-phenoxy-6-(3-phenyl-acryloyl)-cyclohex-2-enone as a yellow solid (220 mg, 43%): 1H NMR (CDCl3) (enol form) δ 2.66 (t, 2H, J=7.2 Hz), 2.84 (t, 2H, J=7.1 Hz), 5.11 (s, 1H), 6.86 (d, 1H, J=15.6 Hz), 7.02 (d, 2H, J=8.1 Hz), 7.20 (m, 2H), 7.28-7.38 (m, 3H). HRMS M+H+ calc: 319.1334, found 319.1340.

Workup

  1. waitAfter 15 min
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with saturated NaCl solution
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0082dd16d90e47f8b732bd10b5c45926
Source dataset
uspto-grants-2003_03
Patent number
US06531491B1

Reaction notes

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