Dimethylformamide → HCID 14297174, compound

HRID 1090915Notes

Reaction equation

HRID 1090915 reaction equation
[Li]CCCC.[Si:6]([C:13]1[O:14][CH:15]=[CH:16][C:17]=1[CH2:18][OH:19])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[Cl-].[Li+].CN(C)[CH:24]=[O:25]>CCCCCC.C(COC)OC>[Si:6]([C:13]1[O:14][CH:15]=[C:16]([CH:24]=[O:25])[C:17]=1[CH2:18][OH:19])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 433294Lithium ChlorideHCID 53250313-Furanmethanol, 2-[(1,1-dimethylethyl)dimethylsilyl]-HCID 178418339Butyllithium

Product 1

HCID 14297174HCID 14297174, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

n-BuLi (a 1.6M solution in hexane; 2.7 ml, 4.28 mmol) was added dropwise to a solution of 3-(2-tert-butyldimethylsilyl-furylmethanol (430 mg, 2.0 mmol) in dimethoxyethane (5 ml) at -78 degrees C. under argon. After stirring at 0 degrees C. for 15 minutes, lithium chloride (860 mg, 20.4 mmol), followed by N,N-dimethylformamide (0.35 ml, 4.48 mmol) was added. Stirring continued at 0 degrees C. for 16 hours and the mixture was quenched with ammonium chloride. Extraction with ethyl acetate and evaporation of the dried (magnesium sulfate) extracts gave a solid, which was recrystallized from hexane to give the titled aldehyde.

Workup

  1. additionwas added
  2. stirringStirring
  3. customcontinued at 0 degrees C
  4. waitfor 16 hours
  5. customthe mixture was quenched with ammonium chloride
  6. extractionExtraction
  7. customwith ethyl acetate and evaporation of the
  8. dry with materialdried (magnesium sulfate)
  9. customextracts gave a solid, which
  10. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-c55500860716451ebabf766b7e87c0c2
Source dataset
uspto-grants-1992_01
Patent number
US05082954

Reaction notes

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