Water → HCID 20458963, compound

HRID 544452Notes

Reaction equation

HRID 544452 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[N:16]2[CH:17]=[CH:18][CH:19]=[C:20]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[C:15]2=[N:14][C:13]=1[CH3:30])=O)C.O.[OH-].[Na+]>O1CCCC1>[F:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][O:21][C:20]1[C:15]2[N:16]([C:12]([CH2:10][OH:9])=[C:13]([CH3:30])[N:14]=2)[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 53732806Ethyl 8-[(2-fluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 20458963HCID 20458963, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled suspension of 1.56 g of lithium aluminium hydride in 200 ml tetrahydrofuran (THF) there was added 15.0 g of 8-(2-fluorobenzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester in portions so that the temperature remained below 10° C. After stirring at 0°-5° C. for an additional 1 hr., 1.6 ml water was added dropwise at 0°-10° C., followed by 1.6 ml15 % aqueous sodium hydroxide and then 4.8 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 200 ml hot tetrahydrofuran and 4×150 ml hot chloroform. The filtrate and washings were combined, evaporated in vacuo, and the solid residue crystallized from acetonitrile to give the desired compound (m.p. 151°-153° C.).

Workup

  1. customremained 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 200 ml hot tetrahydrofuran and 4×150 ml hot chloroform
  6. customevaporated in vacuo
  7. customthe solid residue crystallized from acetonitrile

Sources & evidence

ORD record
ord-9225274f7bda4a9283f8122184f2fe5b
Source dataset
uspto-grants-1984_05
Patent number
US04450164

Reaction notes

Loading…