Acetone → HCID 86696721, compound

HRID 2365865Notes

Reaction equation

HRID 2365865 reaction equation
N1CCC[C@H]1C(O)=O.[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][C:11]=1[F:18].[Cl-].[NH4+].[CH3:21][C:22]([CH3:24])=[O:23]>>[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]([OH:15])[CH2:21][C:22](=[O:23])[CH3:24])=[CH:12][C:11]=1[F:18]

Participants

5

Reactant 4

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 145742L-ProlineHCID 27249854-Chloro-3-Fluorobenzaldehyde

Product 1

HCID 86696721HCID 86696721, compoundYield 73%

Procedure

Proline (23 mg, 0.20 mmol) was added to a solution of 4-chloro-3-fluorobenzaldehyde (159 mg, 1.00 mmol) in acetone (2.5 mL). The resulting mixture was stirred at room temperature overnight. The reaction mixture was then treated with saturated ammonium chloride. After partitioning, the aqueous layer was extracted with ethyl acetate (3×25 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1:4) to afford 4-(4-chloro-3-fluorophenyl)-4-hydroxybutan-2-one (160 mg, 73% yield) as a solid. 1H NMR (500 MHz, CDCl3) δ 7.36 (m, 1H), 7.19 (m, 1H), 7.06 (m, 1H), 5.13 (t, J=6.5 Hz, 1H), 3.43 (br s, 1H), 2.82 (d, J=6.5 Hz, 1H), 2.21 (s, 3H).

Workup

  1. customAfter partitioning
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×25 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with ethyl acetate/petroleum ether (1:4)

Sources & evidence

ORD record
ord-7fb16d2a46834101a9164b662f05bf0e
Source dataset
uspto-grants-2014_04
Patent number
US08697715B2

Reaction notes

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