Benzaldehyde → HCID 58310954, compound

HRID 1189570Notes

Reaction equation

HRID 1189570 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#N.[Na+].[F:12][C:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21](=[O:23])[CH3:22])=[CH:15][CH:14]=1.O>CN(C=O)C>[F:12][C:13]1[CH:14]=[CH:15][C:16]([CH:19]([CH2:20][C:21](=[O:23])[CH3:22])[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 8929Sodium CyanideHCID 57028883-Buten-2-one,4-(4-fluorophenyl)-

Product 1

HCID 58310954HCID 58310954, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of benzaldehyde (1.650 ml, 16.32 mmol) in DMF (5 ml) was added dropwise over the course of ½ hour to a mixture of sodium cyanide (0.401 g, 8.17 mmol) in DMF (20 ml) at 35° C. Stirring was then continued for 1.5 hours at 35° C. A solution of (E)-4-(4-fluorophenyl)but-3-en-2-one (2.0 g, 12.18 mmol) and DMF (10 ml) was then slowly added dropwise over the course of 3.5 hours at 35° C. Stirring was then continued for 3.5 hours at the same temperature. The reaction mixture was treated with twice its volume of water and extracted with DCM. The combined extracts were washed with water and brine, dried with Na2SO4, filtered and concentrated to give a liquid, which was further purified by chromatography on silica gel using an automated Biotage system and EtOAc/Hex (0-50%) to give 2-(4-fluorophenyl)-1-phenylpentane-1,4-dione (1.5 g, 5.55 mmol, 45.6% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.95-7.93 (m, 2H), 7.50-7.46 (m, 1H), 7.40-7.32 (m, 3H), 7.26-7.21 (m, 3H), 5.11 (dd, 1H), 3.59 (dd, 1H), 2.76 (dd, 1H), 2.19 (s, 3H).

Workup

  1. stirringStirring
  2. waitwas then continued for 3.5 hours at the same temperature
  3. extractionextracted with DCM
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a liquid, which
  9. customwas further purified by chromatography on silica gel using an automated Biotage system and EtOAc/Hex (0-50%)

Sources & evidence

ORD record
ord-0a7b70da95f740c2b8b7532eb587c21a
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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