Diethyl Ether → 1-(t-Butyldimethylsilyl)oxymethyl-4-methoxymethoxy-5-methyl-3-naphthalenecarbaldehyde

HRID 654682Notes

Reaction equation

HRID 654682 reaction equation
CCCCCC.C([Li])CCC.C[CH2:13][O:14]CC.[Si:17]([O:24][CH2:25][C:26]1[C:35]2[C:30](=[C:31]([CH3:36])[CH:32]=[CH:33][CH:34]=2)[C:29]([O:37][CH2:38][O:39][CH3:40])=[CH:28][CH:27]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CN(C)C=O>[Si:17]([O:24][CH2:25][C:26]1[C:35]2[C:30](=[C:31]([CH3:36])[CH:32]=[CH:33][CH:34]=2)[C:29]([O:37][CH2:38][O:39][CH3:40])=[C:28]([CH:13]=[O:14])[CH:27]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8058HexaneHCID 149864551-(t-Butyldimethylsilyl)oxymethyl-4-methoxymethoxy-5-methylnaphthaleneHCID 178418339Butyllithium

Product 1

HCID 149864561-(t-Butyldimethylsilyl)oxymethyl-4-methoxymethoxy-5-methyl-3-naphthalenecarbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

52 ml of a hexane solution of 1.6M n-butyl lithium was dropped in an absolute ether (110 ml) solution of 19 g of 1-(t-butyldimethylsilyl)oxymethyl-4-methoxymethoxy-5-methylnaphthalene and agitated for 1 hour. After ice cooling, 8.5 ml of N,N-dimethylformamide was dropped in the reaction solution and the ice bath was removed, followed by agitation for 1 hour until room temperature was reached. Iced water was added to the reaction solution, followed by extraction with ethyl acetate. The resultant organic phase was washed with a saturated saline solution and dried with anhydrous magnesium sulfate. After removal of the solvent by distillation, the residue was purified by silica gel column chromatography (2% ethyl acetate/hexane) to obtain 14.1 g of the captioned compound as a brown oily substance.

Workup

  1. customthe ice bath was removed
  2. waitfollowed by agitation for 1 hour until room temperature
  3. additionIced water was added to the reaction solution
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe resultant organic phase was washed with a saturated saline solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customAfter removal of the solvent
  8. distillationby distillation
  9. customthe residue was purified by silica gel column chromatography (2% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9248cd1f7f604f69b95d3792fc225f86
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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