Potassium bisulfate → 1-(2-Naphthylmethyl)-1H-imidazol-5-ylacetaldehyde

HRID 267083

Reaction equation

HRID 267083 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CON(C)[C:10](=[O:28])[CH2:11][C:12]1[N:16]([CH2:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)[CH:15]=[N:14][CH:13]=1.S(=O)(=O)(O)[O-].[K+]>O1CCCC1.O>[CH:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[CH:27][C:18]=1[CH2:17][N:16]1[C:12]([CH2:11][CH:10]=[O:28])=[CH:13][N:14]=[CH:15]1

Participants

6

Reactant 3

HCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 86751125N-Methoxy-N-methyl-1-(2-naphthylmethyl)-1H-imidazol-5-ylacetamide

Product 1

HCID 867511261-(2-Naphthylmethyl)-1H-imidazol-5-ylacetaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (40.8 mg, 1.07 mmol) in tetrahydrofuran (5 ml) at -45° C. was added a solution of N-methoxy-N-methyl-1-(2-naphthylmethyl)-1H-imidazol-5-ylacetamide (243 mg, 0.895 mmol) in tetrahydrofuran (5 ml) via cannula at such a rate to maintain the temperature at <-35° C. After the addition was complete, the reaction was allowed to warm to +5° C. and then recooled to -35° C. To this solution was added a solution of potassium bisulfate (272 mg) in water (1 ml). The mixture was stirred for 30 min at room temperature and then filtered through celite. The celite pad was washed with ethyl acetate (25 ml). The combined filtrates were washed with sat. sodium bicarbonate (10 ml) and then water (10 ml). The organic layer was dried (MgSO4), filtered and evaporated in vacuo to give 30 as a clear oil. This material was used as is in the next step.

Workup

  1. temperatureto maintain the temperature at <-35° C
  2. additionAfter the addition
  3. temperatureto warm to +5° C.
  4. customrecooled to -35° C
  5. filtrationfiltered through celite
  6. washThe celite pad was washed with ethyl acetate (25 ml)
  7. washThe combined filtrates were washed with sat. sodium bicarbonate (10 ml)
  8. dry with materialThe organic layer was dried (MgSO4)
  9. filtrationfiltered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-c40edfa1df2e4e099f9e647045e9a01b
Source dataset
uspto-grants-1997_07
Patent number
US05652257

Linked notes

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