1-Naphthaldehyde → HCID 53411263, compound

HRID 2361959Notes

Reaction equation

HRID 2361959 reaction equation
[C:1]1([CH:11]=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[CH2:17][NH2:18])[CH3:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[CH2:17][NH:18][CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH3:14]

Participants

6

Reactant 3

HCID 61951-NaphthaldehydeHCID 695242,2-DiethoxyethylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 53411263HCID 53411263, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-naphthaldehyde (2.2 ml, 16.0 mmol) in tetrahydrofuran (6 ml) was added 2,2-diethoxyethanamine (2.9 ml, 20.0 mmol) and the mixture was stirred at room temperature 0.5 hr. And then sodium triacetoxyborohydride (10.6 g, 50 mmol) was added and the mixture was stirred for additional 4 hr. The reaction mixture was diluted with ethyl acetate (200 ml) and washed with saturated aqueous sodium bicarbonate (200 ml), water (200 ml) and brine (200 ml). The organic layer was dried over magnesium sulfate (5 g) and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=100:0 to 70:30) to obtain the title compound (3.0 g, 46%).

Workup

  1. stirringthe mixture was stirred for additional 4 hr
  2. washwashed with saturated aqueous sodium bicarbonate (200 ml), water (200 ml) and brine (200 ml)
  3. dry with materialThe organic layer was dried over magnesium sulfate (5 g)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=100:0 to 70:30)

Sources & evidence

ORD record
ord-fecd15c71bc74a95b9b0c7706993d5e8
Source dataset
uspto-grants-2014_04
Patent number
US08691819B2

Reaction notes

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