Acetic Acid → HCID 86626026, compound

HRID 870387Notes

Reaction equation

HRID 870387 reaction equation
[CH2:1]([NH:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][C:10]([O:15][S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17])=[CH:11][CH:12]=2)[O:7][CH2:6]1)[CH2:2][CH3:3].[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl.O>[CH2:23]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][C:10]([O:15][S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17])=[CH:11][CH:12]=2)[O:7][CH2:6]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 86626025HCID 86626025, compound

Product 1

HCID 86626026HCID 86626026, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Trifluoro-methanesulfonic acid 3-propylamino-chroman-7-yl ester (1.62 g, 4.78 mmol) and benzaldehyde (975 μl, 9.56 mmol) were dissolved in dichloromethane (60 ml). Acetic acid (710 μl, 12.37 mmol) and sodium trisacetoxyborohydride (3.04 g, 14.34 mmol) were sequentially added to the reaction mixture and stirred over the weekend at room temperature. Dichloromethane and water were added to the reaction mixture. The aqueous phase was adjusted to a pH=6 with a 1 molar solution of NaOH. The organic phase was separated, dried over magnesium sulfate, filtered, and evaporated to dryness to yield the crude product. The crude product was purified by chromatography on silica gel using cyclohexane/ethyl acetate (100:0 to 95:5) as eluent, yielding the purified product (1.24 g, 50% purity, 30% yield).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-d708f37233ea4db6933403c7f071c8b8
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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