Acetic Acid → 8-Benzyloxy-3-(3-carboxy-2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine

HRID 4307Notes

Reaction equation

HRID 4307 reaction equation
[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:15]([CH2:19][O:20][CH2:21][C:22]#[CH:23])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:29](=[O:31])=[O:30].C(O)(=O)C>O1CCCC1.CCCCCC>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:15]([CH2:19][O:20][CH2:21][C:22]#[C:23][C:29]([OH:31])=[O:30])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 280Carbon DioxideHCID 138259158-Benzyloxy-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridineHCID 178418339Butyllithium

Product 1

HCID 201523228-Benzyloxy-3-(3-carboxy-2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridineYield 58.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 8-benzyloxy-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine (1 g) in tetrahydrofuran (10 ml) was added dropwise 10% solution of n-butyllithium in n-hexane (2.09 ml) at -60° C. under a nitrogen atmosphere. After being stirred for 10 minutes the solution was treated with dry ice (1.4 g), allowed to warm to room temperature, and acidified with diluted acetic acid. The resulting precipitates were collected by filtration, washed with water, and recrystallized from methanol to give 8-benzyloxy-3-(3-carboxy-2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine (0.67 g).

Workup

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration
  3. washwashed with water
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-3372c0ca9f334c538c916228292e2cfe
Source dataset
uspto-grants-1988_02
Patent number
US04725601

Reaction notes

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