Dichloromethane → 3-Benzyloxy-7-hexyl-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one

HRID 1819537Notes

Reaction equation

HRID 1819537 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6].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.C(Cl)Cl>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]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[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

8

Reactant 4

HCID 6344DichloromethaneHCID 115971-HexeneHCID 789669-Borabicyclo(3.3.1)nonaneHCID 578872943-Benzyloxy-7-iodo-2-(3,4,5-trimethoxy-phenyl)chromen-4-one

Product 1

HCID 578873573-Benzyloxy-7-hexyl-2-(3,4,5-trimethoxy-phenyl)-chromen-4-oneYield 24.8%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 8028TetrahydrofuranSolvent3×HCID 14798Sodium HydroxideSolvent

Procedure

To a stirring solution of 1-hexene (0.109 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 and stirred for 8 hours then 34 (0.505 g, 0.9 mmol) (produced as described in Example 2) in tetrahydrofuran (5 ml), 3M NaOH solution (1.1 ml) and dichloropalladium (dppf) (0.032 g, 0.04 mmol, 0.04 eq) were added and the reaction heated to reflux for 15 hours. The reaction was then quenched with water and diethyl ether. The organic layer was collected and the aqueous layer extracted with dichloromethane. The combined organic layers were dried (MgSO4) and concentrated in vacuo to give a brown oil. Column chromatography (silica gel, DCM) yielded 39e (0.112 g, 24%) as a colourless 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. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give a brown oil

Sources & evidence

ORD record
ord-f0d4c17c64994aa49328041f1a63085e
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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