Pyridine → HCID 20343304, compound

HRID 2050083Notes

Reaction equation

HRID 2050083 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.C(Cl)Cl.[CH3:25][CH:26]([CH3:44])[CH:27]([C:31]1[CH:36]=[CH:35][C:34]([O:37][C:38]([F:43])([F:42])[CH:39]([F:41])[F:40])=[CH:33][CH:32]=1)[C:28](Cl)=[O:29]>CCOCC>[CH:26]([CH:27]([C:31]1[CH:36]=[CH:35][C:34]([O:37][C:38]([F:42])([F:43])[CH:39]([F:40])[F:41])=[CH:33][CH:32]=1)[C:28]([O:12][CH2:11][C:10]1[CH:13]=[CH:14][CH:15]=[C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=1)=[O:29])([CH3:44])[CH3:25]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344Dichloromethane2×HCID 262953-Phenoxybenzyl alcoholHCID 20343321HCID 20343321, compound

Product 1

HCID 20343304HCID 20343304, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred mixture of 6.81 g (0.0340 mol) of m-phenoxybenzyl alcohol, 3.0 ml (2.95 g, 0.0372 mol) of dried pyridine, and 20 ml of methylene chloride is added over a period of 20 minutes a 20 ml methylene chloride solution of 10.6 g (0.034 mol) of 3-methyl-2-[p-(1,1,2,2-tetrafluoroethoxy)phenyl]butyryl chloride. The reaction mixture is stirred at room temperature for 66 hours and then diluted with 200 ml of ether. The ether solution is washed with 200 ml of 20% hydrochloric acid and 200 ml of water, dried with sodium sulfate, filtered, and then evaporated to give 16.24 g (100%). This product is purified on a silica gel dry column (116 cm×5 cm, eluent=1:1 hexane-methylene chloride) by collecting a sample between 85 cm and 63 cm (solvent front=113 cm) to give 12.60 g (78%) of a clear slightly yellow colored oil.

Workup

  1. washThe ether solution is washed with 200 ml of 20% hydrochloric acid and 200 ml of water
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto give 16.24 g (100%)
  6. customThis product is purified on a silica gel
  7. dry with materialdry column (116 cm×5 cm, eluent=1:1 hexane-methylene chloride)
  8. customby collecting a sample between 85 cm and 63 cm (solvent front=113 cm)
  9. customto give 12.60 g (78%) of a clear slightly yellow colored oil

Sources & evidence

ORD record
ord-9a0c12473a2a4e2d99e72993a45af95a
Source dataset
uspto-grants-1980_04
Patent number
US04199595

Reaction notes

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