Dichloromethane → HCID 22563213, compound

HRID 982709Notes

Reaction equation

HRID 982709 reaction equation
[CH:1]([C:3]1[S:11][C:10]2[C:9](=[O:12])[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][N:6]([CH3:18])[C:5]=2[CH:4]=1)=[O:2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+].C(Cl)Cl>ClCCCl>[OH:2][CH2:1][C:3]1[S:11][C:10]2[C:9](=[O:12])[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][N:6]([CH3:18])[C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 22563226HCID 22563226, compound

Product 1

HCID 22563213HCID 22563213, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of ethyl 2-formyl-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate (1.0 g, 3.8 mmol) in 1,2-dichloroethane (23 mL) was added sodium triacetoxyborohydride (1.6 g, 7.5 mmol). The reaction was stirred at room temperature for 24 hours. The reaction was poured into sat. aq. sodium bicarbonate (50 mL) and methylene chloride (30 mL), before it was quenched with water (50 mL). The mixture was allowed to stand at 0° C. overnight. The solid ppt. was collected by vacuum filtration and washed with water. Drying in vacuo yielded an off-white solid (0.36 g, 36%). The filtrate was concentrated to near dryness and diluted with water (20 mL). Filtration followed by treatment with high vacuum gave a second crop of product (0.45 g).

Workup

  1. customwas quenched with water (50 mL)
  2. waitto stand at 0° C. overnight
  3. filtrationwas collected by vacuum filtration
  4. washwashed with water
  5. customDrying in vacuo

Sources & evidence

ORD record
ord-6fba5e08420e4ade8c78288a2ed79e9d
Source dataset
uspto-grants-2005_03
Patent number
US06861438B2

Reaction notes

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