Acetic Acid → HCID 14103612, compound

HRID 870384Notes

Reaction equation

HRID 870384 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][C:8](=O)[CH2:9][O:10]2)=[CH:5][CH:4]=1.[CH2:14]([NH2:17])[CH2:15][CH3:16].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl.O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH:8]([NH:17][CH2:14][CH2:15][CH3:16])[CH2:9][O:10]2)=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 7852PropylamineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 117690977-methoxychroman-3-one

Product 1

HCID 14103612HCID 14103612, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

7-Methoxy-chroman-3-one (1.47 g, 8.25 mmol) and propylamine (748 μl, 9.07 mmol) were dissolved in dichloromethane (20 ml). Acetic acid (710 μl, 12.37 mmol) and sodium trisacetoxyborohydride (3.5 g, 16.51 mmol) were sequentially added to the reaction mixture and the mixture was stirred for 1 hour at room temperature. To the reaction mixture was added dichloromethane and water. The aqueous phase was made alkaline with a 1 molar solution of NaOH. The aqueous phase was separated and extracted (3 times) with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered, and evaporated to dryness to yield the crude product (1.68 g, 92% yield).

Workup

  1. customThe aqueous phase was separated
  2. extractionextracted (3 times) with dichloromethane
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-56590e28f61d41d894e30d525ba54896
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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