4-Bromostyrene → HCID 89581196, compound

HRID 1501186Notes

Reaction equation

HRID 1501186 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH2:9])=[CH:4][CH:3]=1.[BH4-].[Na+].[O:12]1[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14]C1>[OH-].[Na+]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:18][CH:15]2[CH2:16][CH2:17][O:12][CH2:14]2)[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 162634-BromostyreneHCID 74956Tetrahydro-4H-pyran-4-olHCID 4311764Sodium borohydride

Product 1

HCID 89581196HCID 89581196, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To the solution of 1-bromo-4-vinylbenzene (500 mg, 2.75 mmol) in tetrahydro-2H-pyran-4-ol (20 mL) was added mercuric trifluoroacetate (1.18 g, 2.75 mmol), the mixture was stirred for 1 hour at room temperature, then at 0° C. 3 mol/L sodium hydroxide (20 mL) was added with vigorous stirring, after 2 minute, sodium borohydride (0.5 mol/L) in sodium hydroxide (20 ml, 3 mol/L) was added. After 12 hours, the mixture was extracted with ethyl acetate (50 mL*3). The organics were washed with water (5×20 mL) and dried with sodium sulfate, the solvent was removed and purified by column chromatography (silica gel, dichloromethane/methanol=20:1). to give 3-(1-(4-bromo phenyl)ethoxy)-tetrahydrofuran (461 mg, 59%) as oil.

Workup

  1. customat 0° C
  2. waitAfter 12 hours
  3. extractionthe mixture was extracted with ethyl acetate (50 mL*3)
  4. washThe organics were washed with water (5×20 mL)
  5. dry with materialdried with sodium sulfate
  6. customthe solvent was removed
  7. custompurified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-e474186d99cc4d8690cde9649f46e381
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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