Tetrahydrofuran → HCID 67248522, compound

HRID 2425315Notes

Reaction equation

HRID 2425315 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].B1C2CCCC1CCC2.C1COCC1.[OH-].[Na+].Br[C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[C:31](=[O:35])[CH2:30][CH2:29]2>>[CH2:1]([C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[C:31](=[O:35])[CH2:30][CH2:29]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 81251-OcteneHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 5206955-Bromo-1-indanone

Product 1

HCID 67248522HCID 67248522, compoundYield 95.3%

Procedure

A Boron complex was first created by adding 1-octene (0.744 g, 6.633 mmol) to a stirring solution of 0.5M 9-BBN in THF (13.27 mL, 6.633 mmol). The reaction was left to stir at room temperature overnight. 3M NaOH (2.34 mL) was then added to the stirring solution followed by the addition of 5-Bromo-indan-1-one (1 g, 4.7 mmol) and Pd(Ph3)4 (0.145 g, 0.126 mmol). The reaction was refluxed for twelve hours. The resulting solution was concentrated and purified using silica gel chromatography eluding with hexanes-EtOAc (9:1). The reaction provided 2 (1.094 g, 4.48 mmol, 95%) as a clear liquid.

Workup

  1. waitThe reaction was left
  2. temperatureThe reaction was refluxed for twelve hours
  3. concentrationThe resulting solution was concentrated
  4. custompurified

Sources & evidence

ORD record
ord-928af27c7e1b4f4c9a9c6240b8d6e3e8
Source dataset
uspto-grants-2011_06
Patent number
US07964649B2

Reaction notes

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