Lithium diisopropylamide mono(tetrahydrofuran) → t-Butyl-[6-(4-methoxy-3-butenyl)-naphthalen-2-yloxy]-dimethyl-silane

HRID 1174002Notes

Reaction equation

HRID 1174002 reaction equation
[Cl-].COC[P+](F)(F)F.C([N-]C(C)C)(C)C.[Li+].[CH2:17]1[CH2:21][O:20][CH2:19][CH2:18]1.[Si:22]([O:29][CH2:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[CH:37]=[C:36](CCC=O)[CH:35]=[CH:34]2)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>C1COCC1>[C:25]([Si:22]([O:29][C:30]1[CH:37]=[CH:36][C:35]2[C:40](=[CH:39][CH:38]=[C:33]([CH2:32][CH2:18][CH:17]=[CH:21][O:20][CH3:19])[CH:34]=2)[CH:31]=1)([CH3:23])[CH3:24])([CH3:27])([CH3:26])[CH3:28]

Participants

5

Reactant 3

HCID 10997623Lithium diisopropylamide mono(tetrahydrofuran)HCID 230791943-(6-t-Butyldimethylsilyloxymethylnaphthalen-2-yl)propionaldehydeHCID 23079267Methoxymethyltrifluorophosphonium chloride

Product 1

HCID 66941419t-Butyl-[6-(4-methoxy-3-butenyl)-naphthalen-2-yloxy]-dimethyl-silane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methoxymethyltrifluorophosphonium chloride (425 mg) was dissolved in anhydrous THF (10 ml). Then, the solution obtained was added with a 2 mol/l lithium diisopropylamide/THF solution (0.619 ml) under ice-cooling, followed by stirring at room temperature for 1 hour. A solution of the compound (296 mg) obtained in Example 121-7 in anhydrous THF was added in this solution, and the whole was stirred overnight at room temperature. After completion of the reaction, distilled water was added to the solution, and the whole was stirred. The solution was extracted with chloroform and the extract was washed with saturated saline solution. The organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off and the residue was then purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (264 mg) (geometrical-isomer mixture) as a yellow oily substance.

Workup

  1. customThen, the solution obtained
  2. temperaturecooling
  3. stirringthe whole was stirred overnight at room temperature
  4. customAfter completion of the reaction
  5. distillationdistilled water
  6. additionwas added to the solution
  7. stirringthe whole was stirred
  8. extractionThe solution was extracted with chloroform
  9. washthe extract was washed with saturated saline solution
  10. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  11. distillationThe solvent was distilled off
  12. customthe residue was then purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-eb553eb46af140399153d7f7cbb1574a
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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