1-Octene → HCID 67247774, compound

HRID 2425330Notes

Reaction equation

HRID 2425330 reaction equation
B([O-])O[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C=CCCCCCC.B1C2CCCC1CCC2.[OH-].[Na+].[C:31]([O:35][C:36]([N:38]1[C:46]2[C:41](=[CH:42][CH:43]=[C:44](Br)[CH:45]=2)[C:40]([CH2:48][OH:49])=[CH:39]1)=[O:37])([CH3:34])([CH3:33])[CH3:32]>C1COCC1>[C:31]([O:35][C:36]([N:38]1[C:46]2[C:41](=[CH:42][CH:43]=[C:44]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH:45]=2)[C:40]([CH2:48][OH:49])=[CH:39]1)=[O:37])([CH3:34])([CH3:33])[CH3:32]

Participants

7

Reactant 5

HCID 81251-OcteneHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 67247845HCID 67247845, compoundHCID 178443689HCID 178443689, compound

Product 1

HCID 67247774HCID 67247774, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An octyl boronate intermediate is generated by adding 1-octene (1.38 g, 14.1 mmol) to a solution of 9-BBN in THF (28.3 mL of a 0.5 M solution, 14.1 mmol). The reaction mixture is stirred at room temperature overnight. An aqueous solution of sodium hydroxide (5.0 mL of a 3.0 M solution) is added, followed by the addition of compound 25 (3.10 g, 10.0 mmol) and Pd[P(Ph)3]4 (0.310 g, 0.270 mmol). The reaction is brought to reflux and maintained for 12 hours under an inert atmosphere. The reaction is cooled, filtered, concentrated in vacuo and the residue purified using silica gel chromatography with hexane/ethyl acetate (75:25) as solvent.

Workup

  1. temperatureto reflux
  2. temperaturemaintained for 12 hours under an inert atmosphere
  3. temperatureThe reaction is cooled
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customthe residue purified

Sources & evidence

ORD record
ord-f3a36aeda49e45f3a2327786bc976811
Source dataset
uspto-grants-2011_06
Patent number
US07964649B2

Reaction notes

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