Aluminium lithium hydride → HCID 178522940, compound

HRID 1978956Notes

Reaction equation

HRID 1978956 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11]([OH:23])=[C:12]3[CH:18]=[C:17]([C:19](OC)=[O:20])[S:16][C:13]3=[N:14][CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11]([OH:23])=[C:12]3[CH:18]=[C:17]([CH2:19][OH:20])[S:16][C:13]3=[N:14][CH:15]=2)=[O:9])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178496975HCID 178496975, compound

Product 1

HCID 178522940HCID 178522940, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl 5-{[(4-chlorobenzyl)amino]carbonyl}-4-hydroxythieno[2,3-b]pyridine-2-carboxylate (0.506 g) from Example No. 33 is dissolved in THF (100 mL) with heating and then the reaction is cooled in an ice bath. To this solution is added a 1.0 M solution of LiAlH4 in THF (2.4 mL). The reaction is allowed to warm to room temperature and is stirred for 2.5 h. The reaction is quenched with water (1 mL), 10% NaOH (1 mL), and H2O (1 mL). The aluminum salts are filtered off and the filtrate is concentrated in vacuo. The resulting yellow oil is purified by column chromatography (CH2Cl2/methanol, 98/2; 95/5). Fractions homogeneous by TLC are combined and concentrated in vacuo to yield 0.254 g (54%) of the title compound as a pale yellow solid.

Workup

  1. temperaturewith heating
  2. temperaturethe reaction is cooled in an ice bath
  3. customThe reaction is quenched with water (1 mL), 10% NaOH (1 mL), and H2O (1 mL)
  4. filtrationThe aluminum salts are filtered off
  5. concentrationthe filtrate is concentrated in vacuo
  6. customThe resulting yellow oil is purified by column chromatography (CH2Cl2/methanol, 98/2; 95/5)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f23fe2abbef94227bd8c105a7e3567c4
Source dataset
uspto-grants-2001_05
Patent number
US06239142B1

Reaction notes

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