Water → 4-({[Tert-butyl(diphenyl)silyl]oxy}methyl)pyridine-2-carbaldehyde

HRID 1881836Notes

Reaction equation

HRID 1881836 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH2:8][O:9][Si:10]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:4][N:3]=1.CCCCCC.C([Li])CCC.CN(C)[CH:40]=[O:41].O>C(OCC)C.O1CCCC1>[Si:10]([O:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH:40]=[O:41])[CH:7]=1)([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 10670102HCID 10670102, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 593314224-({[Tert-butyl(diphenyl)silyl]oxy}methyl)pyridine-2-carbaldehydeYield 29%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-4-({[tert-butyl(diphenyl)silyl]oxy}methyl)pyridine (8.50 g) in diethyl ether (80 mL) was slowly added a 1.6M n-butyllithium hexane solution (13.0 mL) at −78° C. The reaction mixture was stirred for 30 min, a solution of N,N-dimethylformamide (1.85 mL) in tetrahydrofuran (20 mL) was added, and the mixture was warmed to room temperature and stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (2.16 g, yield 29%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio). MS: 376 (MH+).

Workup

  1. stirringstirred for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8cb2a77c1c004af1b910e0ca79199598
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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