1-Decene → HCID 57887348, compound

HRID 1819556Notes

Reaction equation

HRID 1819556 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].B1C2CCCC1CCC2.[OH:20][C:21]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[C:27](I)[CH:28]=2)[O:23][C:22]=1[C:33]1[CH:38]=[C:37]([O:39][CH3:40])[C:36]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[C:35]([O:49][CH3:50])[CH:34]=1>O1CCCC1.[OH-].[Na+]>[OH:20][C:21]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH:28]=2)[O:23][C:22]=1[C:33]1[CH:38]=[C:37]([O:39][CH3:40])[C:36]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[C:35]([O:49][CH3:50])[CH:34]=1

Participants

6

Reactant 3

HCID 133811-DeceneHCID 789669-Borabicyclo(3.3.1)nonaneHCID 57887339HCID 57887339, compound

Product 1

HCID 57887348HCID 57887348, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 14798Sodium HydroxideSolvent

Procedure

To a stirring solution of 1-decene (0.189 g, 1.3 mmol, 1.4 eq) in tetrahydrofuran (2 ml) under argon was added 9-BBN in tetrahydrofuran (0.5M, 2.8 ml, 1.4 mmol, 1.5 eq). The reaction was stirred for 8 hours then 3-hydroxy-6-iodo-2-(4-benzyloxy-3,5-dimethoxy-phenyl)-chromen-4-one 56 (0.501 g, 0.9 mmol) in tetrahydrofuran (5 ml), 3M NaOH solution (1.26 ml) and dichloropalladium(dppf) (0.021 g, 0.03 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 diethyl ether (2×). The combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo to give a red oil. This was passed through a short plug of silica, eluting with ethyl acetate to give 3-hydroxy-6-decyl-2-(4-benzyloxy-3,5-dimethoxy-phenyl)-chromen-4-one 58(0.369 g, 72%) as 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 diethyl ether (2×)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto give a red oil
  10. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-2286699387ca40c7a93922dfe67149b3
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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