Acetic Acid → HCID 23321861, compound

HRID 280219Notes

Reaction equation

HRID 280219 reaction equation
[C:1]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][CH2:9][C:10]2[N:15]3[CH:16]=[N:17][CH:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)(O)=[O:2].C(O)(=O)C.CO>O1CCCC1>[OH:2][CH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH2:9][C:10]2[N:15]3[CH:16]=[N:17][CH:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 23321885HCID 23321885, compound

Product 1

HCID 23321861HCID 23321861, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-(p-carboxyphenethyl)-imidazo[1,5-a]pyridine (2.66 g) is dissolved in 100 ml of dry tetrahydrofuran at 0° and 20 ml of 1M borane tetrahydrofuran complex in tetrahydrofuran (20 ml) is added dropwise. The reaction mixture is stirred at room temperature for two hours, and 20 ml of acetic acid and 20 ml of methanol are added carefully. The mixture is refluxed for 1 hour, cooled and evaporated, the resulting oil is partitioned between ether and 1N sulfuric acid. The aqueous phase is separated, adjusted to pH=8 and extracted with ethyl acetate the extract is dried over sodium sulfate and evaporated to yield 5-[p-(hydroxymethyl)phenethyl]imidazo[1,5-a]pyridine.

Workup

  1. temperatureThe mixture is refluxed for 1 hour
  2. temperaturecooled
  3. customevaporated
  4. customthe resulting oil is partitioned between ether and 1N sulfuric acid
  5. customThe aqueous phase is separated
  6. extractionextracted with ethyl acetate the extract
  7. dry with materialis dried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-91c2d0dbcc8e4a9c9d6bc576b07db030
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

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