Sodium Thiosulfate → 2-[5-(4-Chloro-benzenesulfonyl)-5-(2,3,6-trifluorophenyl)-pentyl]-oxirane

HRID 564312Notes

Reaction equation

HRID 564312 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:18]2[C:23]([F:24])=[CH:22][CH:21]=[C:20]([F:25])[C:19]=2[F:26])[CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH2:17])(=[O:10])=[O:9])=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:32].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:18]2[C:23]([F:24])=[CH:22][CH:21]=[C:20]([F:25])[C:19]=2[F:26])[CH2:12][CH2:13][CH2:14][CH2:15][CH:16]2[CH2:17][O:32]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 589500547-(4-Chloro-benzenesulfonyl)-7-(2,3,6-trifluoro-phenyl)-1-heptene

Product 1

HCID 589500532-[5-(4-Chloro-benzenesulfonyl)-5-(2,3,6-trifluorophenyl)-pentyl]-oxirane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

[7-(4-chloro-benzenesulfonyl)-7-(2,3,6-trifluoro-phenyl)-1-heptene (0.65 g, 1.6 mmole) and mCPBA (77%, 0.71 g, 3.2 mmole) were stirred in 50 mL DCM for 5 hours. 2 g Na2S2O3 in 100 mL water were added to quench excess mCPBA. The organic layer was separated, washed with 1N NaOH solution (50 mL), brine (50 mL), dried over Na2SO4 and concentrated. The product was purified by column chromatography using EtOAc/Hexane as eluent (Gradient from 0/100 to 40/60 in 40 minute, 0.52 g, 77%). 1H NMR (CDCl3, 400 MHz) δ 7.63 (d, j=8.05 Hz, 2H), 7.45 (d, j=8.05 Hz, 2H), 7.15 (m, 1H), 6.83 (m, 0.5H), 6.74 (m, 0.5H), 4.58 (dd, j=5.1 and 6.5 Hz, 1H), 2.84 (m, 1H), 2.71 (t, j=4.4 Hz, 1H), 2.41 (dd, j=2.9 and 5.1 Hz), 2.45 (m, 1H), 2.34 (m, 1H), 1.25-1.55 (m, 6H).

Workup

  1. customto quench excess mCPBA
  2. customThe organic layer was separated
  3. washwashed with 1N NaOH solution (50 mL), brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe product was purified by column chromatography
  7. custom(Gradient from 0/100 to 40/60 in 40 minute, 0.52 g, 77%)

Sources & evidence

ORD record
ord-8c6e19bbea0d47debec537ea21235d90
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

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