5-(p-Ethoxycarbonylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine → 5-(p-Hydroxymethylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

HRID 477990Notes

Reaction equation

HRID 477990 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[N:17]3[CH:18]=[N:19][CH:20]=[C:16]3[CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl.C1(C)C=CC=CC=1>[OH:3][CH2:4][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[N:17]3[CH:18]=[N:19][CH:20]=[C:16]3[CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 136882135-(p-Ethoxycarbonylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridineHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 136882185-(p-Hydroxymethylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.40 g of 5-(p-ethoxycarbonylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine in 20 ml of methylene chloride is cooled to -70° under nitrogen and 4.0 ml of a 1.543M diisobutylaluminium hydride solution in toluene is added dropwise. The reaction mixture is allowed to warm to room temperature, quenched with 3.2 ml of methanol and 15 ml of water and filtered through Celite®. The layers are separated, the organic one is dried over sodium sulfate and evaporated to yield the title compound, m.p. 142°-145°.

Workup

  1. customquenched with 3.2 ml of methanol and 15 ml of water
  2. filtrationfiltered through Celite®
  3. customThe layers are separated
  4. dry with materialthe organic one is dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-fd4d3332235144f1b76d0d4824ed836a
Source dataset
uspto-grants-1989_12
Patent number
US04889861

Reaction notes

Loading…