Trimethylsilyldiazomethane → HCID 178450050, compound

HRID 480460Notes

Reaction equation

HRID 480460 reaction equation
[OH:1][C:2]([C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[CH:36]=[C:35]([C:40]#[N:41])[CH:34]=[CH:33]2)([C:6]1[N:7]=[CH:8][N:9](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:10]=1)[CH:3]([CH3:5])[CH3:4].C([Li])CCC.C[Si]([CH:51]=[N+:52]=[N-:53])(C)C>C1COCC1.CCCCCC.[Cl-].[NH4+]>[NH:9]1[CH:10]=[C:6]([C:2]([C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[C:35]([C:40]4[N:41]=[N:53][NH:52][CH:51]=4)[CH:36]=3)[CH:31]=2)([OH:1])[CH:3]([CH3:4])[CH3:5])[N:7]=[CH:8]1

Participants

7

Reactant 3

HCID 167693TrimethylsilyldiazomethaneHCID 18769121HCID 18769121, compoundHCID 178418339Butyllithium

Product 1

HCID 178450050HCID 178450050, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To an solution of 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthonitrile in THF (15 mL) was added a solution of n-butyllithium in hexane (1.6M:2.57 mL) under ice cooling, and the mixture was stirred for 20 min. A solution of trimethylsilyldiazomethane in THF (10% wt.:6.0 g) was added dropwise to the mixture and stirred for 90 min under ice cooling. The reaction mixture was diluted with saturated aq. ammonium chloride and extracted with ethyl acetate. The extract was washed with water and brine, dried and concentrated. The residue was purified by column chromatography (eluent; hexane:THF=1:1) and crystallized from ethyl acetate-hexane (1:1) to give the titled compound (881 mg) as a colorless powder.

Workup

  1. stirringstirred for 90 min under ice cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (eluent; hexane:THF=1:1)
  7. customcrystallized from ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-b734e7a55e944f6fa09e1a1921fe2260
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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