Pyridine → 3,3-Bis(4-fluorophenyl)propanal

HRID 2190302Notes

Reaction equation

HRID 2190302 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.N1C=CC=CC=1>CS(C)=O.CCOCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[CH2:9][CH:10]=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 8471TriethylamineHCID 197832883,3-Bis(4-fluorophenyl)propanol

Product 1

HCID 183626473,3-Bis(4-fluorophenyl)propanal

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3,3-bis(4-fluorophenyl)propan-1-ol, prepared in the previous step, in DMSO (100 mL) at room temperature was added triethylamine (13.1 g, 129 mmol, 18 mL) and SO3.pyridine (4.52 g, 28.4 mmol). The reaction mixture was stirred at room temperature for 30 min, diluted with Et2O, washed with water (1×), saturated NH4Cl (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 5% to 40% EtOAc in hexanes) gave 3,3-bis(4-fluorophenyl)propanal.

Workup

  1. washwashed with water (1×), saturated NH4Cl (1×), brine (1×)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography on silica gel (eluted with 5% to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-fc3bf366b6b24be9bff7f08f36df4394
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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