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

HRID 1047490Notes

Reaction equation

HRID 1047490 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, 0.5), 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-2abb4ff1f1c64703921da8156fcaa832
Source dataset
uspto-grants-2013_10
Patent number
US08569521B2

Reaction notes

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