3-(cyclopentyloxy)benzaldehyde → HCID 15453531, compound

HRID 1700869Notes

Reaction equation

HRID 1700869 reaction equation
[CH:1]([O:4][C:5]1[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=1[O:7][CH2:8][CH2:9][NH2:10])([CH3:3])[CH3:2].[CH:15]1([O:20][C:21]2[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=2)[CH:24]=O)[CH2:19][CH2:18][CH2:17][CH2:16]1.[BH4-].[K+]>C1(C)C=CC=CC=1>[CH:15]1([O:20][C:21]2[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=2)[CH2:24][NH:10][CH2:9][CH2:8][O:7][C:6]2[CH:11]=[CH:12][CH:13]=[CH:14][C:5]=2[O:4][CH:1]([CH3:3])[CH3:2])[CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 8199813-(cyclopentyloxy)benzaldehydeHCID 4192641Potassium borohydrideHCID 15453530HCID 15453530, compound

Product 1

HCID 15453531HCID 15453531, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

0.5 g of 2-(2-isopropoxyphenoxy)ethylamine (2.56 mmol) and 0.49 [lacuna] of 3-cyclopentyloxybenzaldehyde (2.56 mmol) are mixed together in 20 ml of toluene. The solution is refluxed for 12 hours, while continuously removing the water formed. The toluene is then evaporated off, the residue is taken up in 20 ml of methanol and the solution is cooled to 0° C. 0.28 g of potassium borohydride (5.12 mmol) is added portionwise and the mixture is stirred for 3 hours at room temperature. The methanol is evaporated off, the residue is taken up in dichloromethane and the organic phase is washed with water and then with saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulfate and filtered, and the solvent is evaporated off under vacuum. The title product is isolated by chromatography on a column of silica (eluent: 98/1.5/0.5 dichloromethane/methanol/aqueous ammonia). 0.77 g of the title product is obtained in the form of a pale yellow oil:

Workup

  1. temperatureThe solution is refluxed for 12 hours
  2. customwhile continuously removing the water
  3. customformed
  4. customThe toluene is then evaporated off
  5. customThe methanol is evaporated off
  6. washthe organic phase is washed with water
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-ca0642067e2d47d3a47e8ed7f0abf932
Source dataset
uspto-grants-2002_02
Patent number
US06350913B1

Reaction notes

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