Water → HCID 58310972, compound

HRID 1189573Notes

Reaction equation

HRID 1189573 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[C-]#N.[Na+].[C:13]1(/[CH:19]=[CH:20]/[C:21](=[O:23])[CH3:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:5](=[O:6])[CH:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:20][C:21](=[O:23])[CH3:22])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 680093-FluorobenzaldehydeHCID 637759Benzylideneacetone

Product 1

HCID 58310972HCID 58310972, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 3-fluorobenzaldehyde (2.005 ml, 18.33 mmol) in DMF (5 ml) was added dropwise over the course of 0.5 hours to a mixture of sodium cyanide (0.450 g, 9.18 mmol) in DMF (20 ml) at 35° C. Stirring was then continued for 1.5 hours at 35° C. A solution of (E)-4-phenylbut-3-en-2-one (2.0 g, 13.68 mmol) in DMF (5 ml) was then slowly added dropwise over the course of 0.5 hours at 35° C. Stirring was 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, purified by chromatography on silica gel using an automated Biotage system (EtOAc/Hex, 0-50%) to give 1-(3-fluorophenyl)-2-phenylpentane-1,4-dione (2.1 g, 7.77 mmol, 56.8% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.75-7.73 (m, 1H), 7.64-7.61 (m, 1H), 7.37-7.12 (m, 7H), 5.03 (dd, 1H), 3.61 (dd, 1H), 2.76 (dd, 1H), 2.19 (s, 3H).

Workup

  1. stirringStirring
  2. waitwas 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
  9. custompurified by chromatography on silica gel using an automated Biotage system (EtOAc/Hex, 0-50%)

Sources & evidence

ORD record
ord-21235340b12341c7aa57e262aa56420f
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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