Dichloromethane → HCID 57887356, compound

HRID 1819543Notes

Reaction equation

HRID 1819543 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].B1C2CCCC1CCC2.[CH2:20]([O:27][C:28]1[C:37](=[O:38])[C:36]2[C:31](=[CH:32][C:33](I)=[CH:34][CH:35]=2)[O:30][C:29]=1[C:40]1[CH:45]=[C:44]([O:46][CH3:47])[C:43]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[C:42]([O:56][CH3:57])[CH:41]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(Cl)Cl>O1CCCC1.[OH-].[Na+].Cl[Pd]Cl>[CH2:20]([O:27][C:28]1[C:37](=[O:38])[C:36]2[C:31](=[CH:32][C:33]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[CH:34][CH:35]=2)[O:30][C:29]=1[C:40]1[CH:45]=[C:44]([O:46][CH3:47])[C:43]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[C:42]([O:56][CH3:57])[CH:41]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 133811-DeceneHCID 789669-Borabicyclo(3.3.1)nonaneHCID 57887335HCID 57887335, compound

Product 1

HCID 57887356HCID 57887356, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 8028TetrahydrofuranSolvent3×HCID 14798Sodium HydroxideSolvent

Procedure

To a stirring solution of 1-decene (0.176 g, 1.3 mmol, 1.4 eq) in tetrahydrofuran (2 ml) under argon was added 9-BBN in tetrahydrofuran (0.5M, 2.7 ml, 1.4 mmol, 1.5 eq). The reaction was stirred for 6 hours then 35 (0.560 g, 0.9 mmol) in tetrahydrofuran (5 ml), 3M NaOH solution (1.1 ml) and dichloropalladium (dppf) (0.027 g, 0.03 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 40 g (0.339 g, 59%) as a pale yellow 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-09d2ddac6ab34361bf6df5d9f1812093
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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