Methanol → 5-(p-Hydroxymethylphenyl)imidazo[1,5-a]pyridine

HRID 280216Notes

Reaction equation

HRID 280216 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]3[CH:18]=[N:19][CH:20]=[C:16]3[CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.CO>C(Cl)Cl>[OH:3][CH2:4][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:17]3[CH:18]=[N:19][CH:20]=[C:16]3[CH:15]=[CH:14][CH:13]=2)=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 13649431ethyl 4-(H-imidazo[1,5-a]pyridin-5-yl)benzoateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 136494325-(p-Hydroxymethylphenyl)imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(p-Ethoxycarbonylphenyl)-imidazo[1,5-a]pyridine (1.0 g) is dissolved in 26 ml of methylene chloride at -78° under nitrogen and 6.6 ml of diisobutylaluminum hydride in toluene (11.4 mmole) is added dropwise. After stirring for 1 hour, 1.5 ml of methanol is added, the cold bath is removed and 15 ml of water is added. The salts are filtered off, the organic phase is dried over sodium sulfate and evaporated to yield 5-(p-hydroxymethylphenyl)imidazo[1,5-a]pyridine, m.p. 137°-138°.

Workup

  1. customthe cold bath is removed
  2. addition15 ml of water is added
  3. filtrationThe salts are filtered off
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-360f3ccc1473485ebb4d511b266555b2
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

Loading…