4-Methyl-1-pentene → 3-Benzyloxy-7-(4-methyl-pentyl)-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one

HRID 1819539Notes

Reaction equation

HRID 1819539 reaction equation
[CH3:1][CH:2]([CH3:6])[CH2:3][CH:4]=[CH2:5].B1C2CCCC1CCC2.[CH2:16]([O:23][C:24]1[C:33](=[O:34])[C:32]2[C:27](=[CH:28][C:29](I)=[CH:30][CH:31]=2)[O:26][C:25]=1[C:36]1[CH:41]=[C:40]([O:42][CH3:43])[C:39]([O:44][CH3:45])=[C:38]([O:46][CH3:47])[CH:37]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCCC1.[OH-].[Na+].Cl[Pd]Cl>[CH2:16]([O:23][C:24]1[C:33](=[O:34])[C:32]2[C:27](=[CH:28][C:29]([CH2:5][CH2:4][CH2:3][CH:2]([CH3:6])[CH3:1])=[CH:30][CH:31]=2)[O:26][C:25]=1[C:36]1[CH:41]=[C:40]([O:42][CH3:43])[C:39]([O:44][CH3:45])=[C:38]([O:46][CH3:47])[CH:37]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 127244-Methyl-1-penteneHCID 789669-Borabicyclo(3.3.1)nonaneHCID 578872943-Benzyloxy-7-iodo-2-(3,4,5-trimethoxy-phenyl)chromen-4-one

Product 1

HCID 578873333-Benzyloxy-7-(4-methyl-pentyl)-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 8028TetrahydrofuranSolvent3×HCID 14798Sodium HydroxideSolvent

Procedure

To a stirring solution of 4-methyl pent-1-ene (0.110 g, 1.3 mmol, 1.4 eq) in tetrahydrofuran (2 ml) under argon at 0° C. was added 9-BBN in tetrahydrofuran (0.5M, 2.7 ml, 1.4 mmol, 1.5 eq). The reaction was allowed to warm to room temperature then stirred for 6 hours then 34 (0.499 g, 0.9 mmol) (prepared as described in Example 2) in tetrahydrofuran (5 ml), 3M NaOH solution (1.1 ml) and dichloropalladium (dppf) (0.028 g, 0.03 mmol, 0.04 eq) were added and the reaction heated to reflux for 14 hours. The reaction was then quenched with water and diethyl ether. The organic layer was collected and the aqueous layer extracted with diethyl ether (2×). The combined organic layers were washed with 1M HCl and brine then dried (MgSO4) and concentrated in vacuo to give a yellow oil. A silica plug (dichloromethane) yielded 39e* (0.197 g, 49%) as a yellow oil.

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 14 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 1M HCl and brine
  7. dry with materialthen dried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto give a yellow oil
  10. customA silica plug (dichloromethane) yielded 39e* (0.197 g, 49%) as a yellow oil

Sources & evidence

ORD record
ord-109930d818c1461cb37fac8de7b56c6d
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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