Methanol → 3-Fluoro-2-(1-trityl-1H-imidazol-4-yl)benzaldehyde

HRID 1774935Notes

Reaction equation

HRID 1774935 reaction equation
[F:1][C:2]1[C:3]([C:12]2[N:13]=[CH:14][N:15]([C:17]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:16]=2)=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](OC)=[O:6].CC(C[AlH]CC(C)C)C.CO.[NH4+].[Cl-]>C1(C)C=CC=CC=1.CCOC(C)=O.[Cl-].[Na+].O>[F:1][C:2]1[C:3]([C:12]2[N:13]=[CH:14][N:15]([C:17]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:16]=2)=[C:4]([CH:9]=[CH:10][CH:11]=1)[CH:5]=[O:6]

Participants

8

Reactant 4

HCID 887MethanolHCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 70874744Methyl 3-fluoro-2-(1-trityl-1H-imidazol-4-yl)benzoate

Product 1

HCID 890529543-Fluoro-2-(1-trityl-1H-imidazol-4-yl)benzaldehyde

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of methyl 3-fluoro-2-(1-trityl-1H-imidazol-4-yl)benzoate (62 mg, 0.134 mmol) in toluene (4 mL) at −78° C. was added dropwise a solution DIBAH (1 M, 0.161 mL, 0.161 mmol) Stirring was continued at for 10 min. At this temperature, dry methanol was added. The mixture was poured into saturated aqueous NH4Cl (5 mL), diluted with EtOAc (15 mL), shaken vigorously for 3 min, added brine (5 mL), shaken again, the phases separated and the organic layer dried over Na2SO4, filtered, and evaporated to give the desired aldehyde which was used without further purification.

Workup

  1. customwas continued at for 10 min
  2. stirringshaken vigorously for 3 min
  3. stirringshaken again
  4. customthe phases separated
  5. dry with materialthe organic layer dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-ba53e2c1376e4664ba7aea1dd6575aa3
Source dataset
uspto-grants-2016_02
Patent number
US09260434B2

Reaction notes

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