Water → [8-(Benzyloxy)imidazo[1,2-a]pyridin-2-yl]methanol

HRID 544455Notes

Reaction equation

HRID 544455 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[N:13]=[C:14]2[C:19]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:18][CH:17]=[CH:16][N:15]2[CH:28]=1)=O)C.O.[OH-].[Na+]>O1CCCC1>[CH2:21]([O:20][C:19]1[C:14]2[N:15]([CH:28]=[C:12]([CH2:10][OH:9])[N:13]=2)[CH:16]=[CH:17][CH:18]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 53472001Ethyl 8-(benzyloxy)imidazo[1,2-a]pyridine-2-carboxylate

Product 1

HCID 20458946[8-(Benzyloxy)imidazo[1,2-a]pyridin-2-yl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled suspension of 1.5 g lithium aluminium hydride in 150 ml tetrahydrofuran there was added 15.0 g 8-benzyloxyimidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester (obtained according to Example 5) in portions so that the temperature remains below 10° C. After stirring at 0°-5° C. for an additional 1hr., 1.5 ml water was added dropwise at 0°-10° C., followed by 1.5 ml 15% aqueous sodium hyroxide and then 4.5 ml water. The mixture was allowed to warm to room temperature with stirring, and was then suction-filtered in a sintered glass funnel. The solids left in the funnelwere thoroughly washed with 4×200 ml hot chloroform.

Workup

  1. customremains below 10° C
  2. stirringwith stirring
  3. filtrationwas then suction-filtered in a sintered glass funnel
  4. waitThe solids left in the funnelwere
  5. washthoroughly washed with 4×200 ml hot chloroform

Sources & evidence

ORD record
ord-a6b66cdc51d343e7ac8064cdf020ee6d
Source dataset
uspto-grants-1984_05
Patent number
US04450164

Reaction notes

Loading…