Tetrahydrofuran → 1-(4-(1,3-Dioxolan-2-yl)phenyl)-2-phenylethanone

HRID 604985Notes

Reaction equation

HRID 604985 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:13]=[CH:12][C:9]([C:10]#N)=[CH:8][CH:7]=1.[CH2:14]([Mg]Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1C[O:26]CC1>>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:13]=[CH:12][C:9]([C:10](=[O:26])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 27784284-(1,3-Dioxolan-2-yl)benzonitrileHCID 178418336HCID 178418336, compound

Product 1

HCID 591643561-(4-(1,3-Dioxolan-2-yl)phenyl)-2-phenylethanone

Procedure

To a solution of 4-(1,3-dioxolan-2-yl)benzonitrile (5.0 g, 28.54 mmol) in anhydrous THF (100 mL) was added benzyl magnesium chloride (36 mL, 20% wt solution in THF, 43 mmol) slowly at 0° C. After one hour the mixture was warmed to room temperature. After four hours the mixture was cooled to 0° C. and quenched with saturated NH4Cl. The mixture was warmed to room temperature and extracted with ethyl acetate (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (10% ethyl acetate/hexanes) gave 1-[4-(1,3-dioxolan-2-yl)phenyl]-2-phenylethanone as a pale yellow solid: 1H-NMR (500 MHz, CDCl3): δ 8.02 (2H, d, J=8.30 Hz), 7.57 (2H, d, J=8.30 Hz), 7.38-7.24 (% H, m), 5.86 (1H, s), 4.29 (2H, s), 4.28-4.09 (4H, m).

Workup

  1. temperatureAfter four hours the mixture was cooled to 0° C.
  2. customquenched with saturated NH4Cl
  3. temperatureThe mixture was warmed to room temperature
  4. extractionextracted with ethyl acetate (3×)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-10df57e3a1dd47cd96f1607e0f4d6ab6
Source dataset
uspto-grants-2011_03
Patent number
US07910561B2

Reaction notes

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