Acetaldehyde → HCID 57934267, compound

HRID 1950633Notes

Reaction equation

HRID 1950633 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]2[CH:28]=[CH:27][CH:26]=[CH:25][C:12]=2[CH2:13][CH:14]2[CH2:23][CH2:22][C:21]3[CH:20]=[C:19]([OH:24])[CH:18]=[CH:17][C:16]=3[CH2:15]2)=[CH:4][CH:3]=1.[C:29](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:30].[Na+].C(=O)C.C(=O)(O)[O-].[Na+]>O1CCCC1.C(O)(=O)C>[CH2:29]([N:10]([CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[C:11]1[CH:28]=[CH:27][CH:26]=[CH:25][C:12]=1[CH2:13][CH:14]1[CH2:23][CH2:22][C:21]2[CH:20]=[C:19]([OH:24])[CH:18]=[CH:17][C:16]=2[CH2:15]1)[CH3:30]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57934063HCID 57934063, compound

Product 1

HCID 57934267HCID 57934267, compoundYield 67.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-{2-[2-(4-hydroxyphenyl)ethylamino]benzyl}-5,6,7,8-tetrahydronaphthalen-2-ol (1.0 g) in tetrahydrofuran (15 ml) were sequentially added acetic acid (in catalytic amounts), sodium triacetoxyborohydride (2.8 g) and acetaldehyde (572 mg), and the solution was stirred overnight at room temperature. To the reaction solution was added a saturated aqueous solution of sodium bicarbonate, the solution was extracted with ethyl acetate, then washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (730 mg).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-0ca7961c4cc54d958af607a854b03a4e
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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