Isobutylene oxide → HCID 60880493, compound

HRID 452643Notes

Reaction equation

HRID 452643 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:11][C:12]1([O:15][CH2:14]1)[CH3:13]>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:11][C:12]([CH3:14])([OH:15])[CH3:13])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11208Isobutylene oxideHCID 24758Sodium hydrideHCID 660494-Bromothiophenol

Product 1

HCID 60880493HCID 60880493, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromothiophenol (9.45 g, 50.0 mmol) in tetrahydrofuran (150 mL) was added sodium hydride (60% in oil, 2.20 g, 55.0 mmol) at 0° C. by small portions, and the resulting mixture was stirred for 1 hr. To this reaction mixture was added isobutylene oxide (4.91 mL, 55.0 mmol), and the resulting mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=1/1) to give the title compound (11.6 g, yield 89%) as a colorless oil.

Workup

  1. stirringthe resulting mixture was stirred overnight at room temperature
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-85f65893c2b94321a0f3681f2d9664f8
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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