Ethanol → HCID 57554862, compound

HRID 1511886Notes

Reaction equation

HRID 1511886 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:19][CH2:18][C:17](=O)[CH2:16]2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:21]([OH:27])(=[O:26])[CH2:22]C(O)=O.C([O-])(=O)C.[NH4+:32].C(O)C.CO>>[NH2:32][C:17]1([CH2:22][C:21]([OH:27])=[O:26])[CH2:18][CH2:19][CH:15]([C:12]2[CH:13]=[CH:14][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:10][CH:11]=2)[CH2:16]1

Participants

6

Reactant 5

HCID 702EthanolHCID 867Malonic AcidHCID 887MethanolHCID 517165Ammonium AcetateHCID 57443795HCID 57443795, compound

Product 1

HCID 57554862HCID 57554862, compound

Conditions

Temperature
80 °C

Procedure

3-(4-Octyl-phenyl)-cyclopentanone, malonic acid (0.076 g, 0.734 mmol), ammonium acetate (0.057 g, 0.734 mmol) were suspended in the mixture of ethanol (1.50 mL, 25.7 mmol) and methanol (0.50 mL, 12.36 mmol) in a 15-mL, 2-necked round-bottomed flask equipped with a condenser. The heterogeneous mixture was heated to reflux at 80° C. for about 24 hours. Heating was removed. The crude mixture was taken up in dichloromethane/water mixture (20 mL/20 mL). The resulting fine suspension was filtered, washed several times with water and dichloromethane, and vacuum-dried to yield 2-(1-amino-3-(4-octylphenyl)cyclopentyl)acetic acid (0.020 g, 0.060 mmol) as off-white solid.

Workup

  1. customequipped with a condenser
  2. temperatureThe heterogeneous mixture was heated
  3. temperatureHeating
  4. customwas removed
  5. filtrationThe resulting fine suspension was filtered
  6. washwashed several times with water and dichloromethane
  7. customvacuum-dried

Sources & evidence

ORD record
ord-391564d96c1f4b70aa9cf0eadbc2d5a7
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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