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

HRID 22543Notes

Reaction equation

HRID 22543 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

1 g of 5-(p-ethoxycarbonylphenyl)imidazo[1,5-a]pyridine is dissolved in 26 ml of methylene chloride at -78° under nitrogen, and then 6.6 ml of diisobutylaluminium hydride in toluene (11.4 mmole) is added dropwise. After stirring for 1 h, 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 the title compound, 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-a75b7f5615474750a3b98cc880b040cc
Source dataset
uspto-grants-1995_06
Patent number
US05428160

Reaction notes

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