HCID 18717979, compound → HCID 22620126, compound

HRID 840619Notes

Reaction equation

HRID 840619 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[N:7]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:8]=[N:9][C:10]=1[Cl:11].[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[Cl:11][C:10]1[N:9]=[CH:8][N:7]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:17])([CH3:18])[CH3:19])[C:6]=1[CH2:5][CH2:4][CH:3]=[O:2]

Participants

4

Reactant 2

HCID 18717979HCID 18717979, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 22620126HCID 22620126, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 0.20 g of 3-[5-chloro-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazol4-yl]-propionic acid methyl ester in 10 mL of toluene cooled to −75° C. under nitrogen was added 0.5 mL of 1.5 M diisobutylaluminum hydride. After 1 h at −75° C., the reaction was quenched with 0.2 mL of methanol, allowed to warm to room temperature over 30 min and partitioned between 1N sodium carbonate and ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The crude 3-[5-chloro-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazol-4-yl]-propionaldehyde (0.2 g) was essentially homogeneous by TLC, eluting with ethyl acetate.

Workup

  1. customthe reaction was quenched with 0.2 mL of methanol
  2. custompartitioned between 1N sodium carbonate and ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-1e0315c97dbd456ca975f66cf505158f
Source dataset
uspto-grants-2002_04
Patent number
US06369076B1

Reaction notes

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