Butylboronic Acid → 3-Benzyloxy-7-butyl-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one

HRID 1819535Notes

Reaction equation

HRID 1819535 reaction equation
[CH2:1](B(O)O)[CH2:2][CH2:3][CH3:4].[CH2:8]([O:15][C:16]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][C:21](I)=[CH:22][CH:23]=2)[O:18][C:17]=1[C:28]1[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCCC1.[OH-].[Na+].Cl[Pd]Cl>[CH2:8]([O:15][C:16]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][C:21]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:22][CH:23]=2)[O:18][C:17]=1[C:28]1[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 2

HCID 20479Butylboronic AcidHCID 578872943-Benzyloxy-7-iodo-2-(3,4,5-trimethoxy-phenyl)chromen-4-one

Product 1

HCID 578873513-Benzyloxy-7-butyl-2-(3,4,5-trimethoxy-phenyl)-chromen-4-oneYield 23.2%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirring solution of n-butane boronic acid (0.133 g, 1.3 mmol, 1.4 equ) and dichloropalladium (dppf) (0.050 g, 0.06 mmol, 0.07 eq) in tetrahydrofuran (7 ml) and 3M NaOH solution (1.1 ml) was added 34 (0.500 g, 0.9 mmol) added and the reaction heated to reflux for 21 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 IM HCl and brine then dried (MgSO4) and concentrated in vacuo to give a yellow oil. A silica plug (dichloromethane) yielded 39d (0.099 g, 23%) as an orange oil.

Workup

  1. additionadded
  2. temperaturethe reaction heated
  3. temperatureto reflux for 21 hours
  4. customThe reaction was then quenched with water and diethyl ether
  5. customThe organic layer was collected
  6. extractionthe aqueous layer extracted with diethyl ether (2×)
  7. washThe combined organic layers were washed with IM HCl and brine
  8. dry with materialthen dried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customto give a yellow oil

Sources & evidence

ORD record
ord-e994810a40874ee991cb10f6a3288956
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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