Ethyl Acetate → HCID 22241626, compound

HRID 892010Notes

Reaction equation

HRID 892010 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18](=[O:20])[CH3:19])[N:13]=[C:12]2[CH2:21][C:22](=[O:24])[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[NH4+].[Cl-].C(OCC)(=O)C>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18](=[O:20])[CH3:19])[N:13]=[C:12]2[CH2:21][CH:22]([OH:24])[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 22241639HCID 22241639, compound

Product 1

HCID 22241626HCID 22241626, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the product from Step A (0.13 g, 0.4 mmol) in methanol (8 ml) was added NaBH4 (0.016 g, 0.4 mmol) and the mixture was stirred at room temperature for 20 min. A saturated aqueous solution of NH4Cl (20 ml) and ethyl acetate (20 ml) were added to the reaction mixture. The aqueous layer was separated and extracted with ethyl acetate (3×15 ml). The combined extracts were washed with a saturated aqueous solution of NaCl (2×15 ml), dried (MgSO4), and evaporated to give an oil (0.12 g). MS(APCl) m/z 325 (M+H)+.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (3×15 ml)
  3. washThe combined extracts were washed with a saturated aqueous solution of NaCl (2×15 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-d9e91e5601a64a0099a0790c638925bf
Source dataset
uspto-grants-2006_02
Patent number
US07005443B1

Reaction notes

Loading…