Diethyl Ether → HCID 66783955, compound

HRID 1096825Notes

Reaction equation

HRID 1096825 reaction equation
[Si]([O:8][C:9]1[C:14]([Cl:15])=[CH:13][C:12]([CH:16]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH3:17])=[CH:11][C:10]=1[Cl:26])(C(C)(C)C)(C)C.CCOCC>CN(C=O)C.O>[Si:19]([O:18][CH:16]([C:12]1[CH:13]=[C:14]([Cl:15])[C:9]([OH:8])=[C:10]([Cl:26])[CH:11]=1)[CH3:17])([C:22]([CH3:25])([CH3:23])[CH3:24])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 66783839HCID 66783839, compound

Product 1

HCID 66783955HCID 66783955, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A sol. of (rac.)-2-(tert-butyldimethylsilanyloxy)-5-[1-(tert-butyldimethylsilanyloxy)ethyl]-1,3-dichlorobenzene (188 mg, 0.432 mmol) and CS2CO3 (76.2 mg, 0.126 mmol) in a mixture of DMF (0.50 mL) and water (50 μL) was stirred at rt overnight. Et2O (75 mL) was added. The sol. was washed with brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification by FC(CH2Cl2) yielded the title compound (122 mg, 88%). LC-MS: tR=1.15 min.

Workup

  1. washThe sol. was washed with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification by FC(CH2Cl2)

Sources & evidence

ORD record
ord-9b614613bef8409f94ed889864e0862a
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

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