Diisobutylaluminumhydride → HCID 59599684, compound

HRID 2266640Notes

Reaction equation

HRID 2266640 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:10]=1[F:11])=O)C.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[F:11][C:10]1[N:9]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:17])([CH3:19])[CH3:18])[CH:8]=[N:7][C:6]=1[CH2:4][OH:3]

Participants

4

Reactant 2

HCID 21225700Diisobutylaluminumhydride2×HCID 59599688HCID 59599688, compound

Product 1

HCID 59599684HCID 59599684, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 5-fluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carboxylic acid ethyl ester (400 mg) in toluene (10 ml) at −78° C. under an argon atmosphere was added dropwise diisobutylaluminium hydride (DIBAL) (1.72 ml; 20 wt % solution in toluene) for 10 minutes (temperature below −75° C.). After 2 hours of stirring at −78° C., conversion of the ester was found to be incomplete. More DIBAL solution (1.17 ml.) was added over a period of 5 minutes and stirring at −78° C. was continued for 1 hour and 30 minutes. The mixture was quenched by the addition of 10 ml potassium-sodium tartrate concentrated aqueous solution. The aqueous phase was back extracted with ethyl acetate. The combined organics were washed with H2O and brine, dried over MgSO4, filtered and concentrated to leave [5-fluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-yl]-methanol as (346 mg) as off-white solid. The crude product was used in the next reaction step without further purification. MS (ISP): 247.3 ([M+H]+).

Workup

  1. stirringstirring at −78° C.
  2. waitwas continued for 1 hour and 30 minutes
  3. customThe mixture was quenched by the addition of 10 ml potassium-sodium tartrate concentrated aqueous solution
  4. extractionThe aqueous phase was back extracted with ethyl acetate
  5. washThe combined organics were washed with H2O and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3c2608bab0714e719d1738c15a08c34c
Source dataset
uspto-grants-2010_12
Patent number
US07858652B2

Reaction notes

Loading…