1-Octene → HCID 57887315, compound

HRID 1819558Notes

Reaction equation

HRID 1819558 reaction equation
C=CCCCCCC.B1[CH:14]2[CH2:15][CH2:16][CH2:17][CH:10]1[CH2:11][CH2:12][CH2:13]2.Br[C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][C:28]=1[CH2:29][CH3:30])[O:25][C:24]([C:31]1[CH:36]=[C:35]([O:37][CH3:38])[C:34]([O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[C:33]([O:47][CH3:48])[CH:32]=1)=[C:23]([OH:49])[C:22]2=[O:50]>O1CCCC1.[OH-].[Na+]>[CH2:29]([C:28]1[CH:27]=[C:26]2[C:21]([C:22](=[O:50])[C:23]([OH:49])=[C:24]([C:31]3[CH:32]=[C:33]([O:47][CH3:48])[C:34]([O:39][CH2:40][C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)=[C:35]([O:37][CH3:38])[CH:36]=3)[O:25]2)=[CH:20][C:19]=1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:10])[CH3:30]

Participants

6

Reactant 3

HCID 81251-OcteneHCID 789669-Borabicyclo(3.3.1)nonaneHCID 57887353HCID 57887353, compound

Product 1

HCID 57887315HCID 57887315, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 14798Sodium HydroxideSolvent

Procedure

To a stirring solution of 1-octene (0.032 g, 0.3 mmol, 1.4 eq) in tetrahydrofuran (1 ml) under argon at 0° C. was added 9-BBN in tetrahydrofuran (0.5M, 0.6 ml, 0.3 mmol, 1.5 eq). The reaction was stirred for 7 hours then 6-bromo-7-ethyl-3-hydroxy-2-(4-benzyloxy-3,5-dimethoxy-phenyl)-chromen-4-one 57 (0.102 g, 0.2 mmol) in tetrahydrofuran (4 ml), 3M NaOH solution (0.2 ml) and dichloropalladium(dppf) (0.005 g, 0.006 mmol, 0.03 eq) were added and the reaction heated to reflux for 15 hours. The reaction was then quenched with water and diethyl ether and acidified (6 M HCl). The organic layer was collected and the aqueous layer extracted with dichloromethane. The combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo to give a red oil.

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 15 hours
  3. customThe reaction was then quenched with water and diethyl ether
  4. customThe organic layer was collected
  5. extractionthe aqueous layer extracted with dichloromethane
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto give a red oil

Sources & evidence

ORD record
ord-2a9a14765f1b412fb1516754d3531ad9
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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