Sodium Methoxide → sodium 4-[(E)-2-(4-fluorophenyl)vinyl]benzenesulfinate

HRID 1351620Notes

Reaction equation

HRID 1351620 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([S:16](CCC#N)(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C[O-].[Na+:25]>C1COCC1.CO.CCCC(C)C.CCOCC>[F:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([S:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[CH:6][CH:7]=1.[Na+:25]

Participants

7

Reactant 2

HCID 10942334Sodium MethoxideHCID 210994903-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)propanenitrile

Product 1

HCID 23712902sodium 4-[(E)-2-(4-fluorophenyl)vinyl]benzenesulfinateYield 96.7%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 78922-MethylpentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)propanenitrile (Step 2, 75 g, 0.24 mol) in THF (1 L) and MeOH (500 mL) was added sodium methoxide (13 g, 0.24 mol). The mixture was stirred for 1 h at room temperature then diluted with isohexane and Et2O. The solid was filtered off, triturated with isohexane and dried under vacuum to give sodium 4-[(E)-2-(4-fluorophenyl)vinyl]benzenesulfinate (66 g). δH (500 MHz, d6 DMSO): 7.65 (2H, t, J 6.8), 7.53 (2H, d, J 7.8), 7.45 (2H, d, J 7.7), 7.26–7.18 (4H, m). m/z (ES−) 261 [(M−Na)−].

Workup

  1. filtrationThe solid was filtered off
  2. customtriturated with isohexane
  3. customdried under vacuum

Sources & evidence

ORD record
ord-d5a22ab9c65042fcaac2a02362dbe661
Source dataset
uspto-grants-2007_05
Patent number
US07217740B2

Reaction notes

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