Octanoic Acid → 4-Cyanobenzaldehyde

HRID 1922334Notes

Reaction equation

HRID 1922334 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH2:11])=[CH:8][CH:7]=1.C(O)(=O)CCCCCCC.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>ClCCl>[C:10]([C:9]1[CH:12]=[CH:13][C:6]([CH:2]=[O:1])=[CH:7][CH:8]=1)#[N:11]

Participants

6

Reactant 4

HCID 379Octanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 10559254(4-(1,3-dioxolan-2-yl)phenyl)methanamine

Product 1

HCID 660424-CyanobenzaldehydeYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 4-(1,3-dioxacyclopent-2-yl)benzylamine is condensed with octanoic acid in dichloromethane in the presence of a peptide coupling system consisting of DCC and HOBt according to a method already described (Ouari O.; Polidori A.; Pucci B.; Tordo P.: Chalier F. J. Org. Chem. 1999, 64, 3554-3556) and then the dioxolane protecting group is removed by treatment in a 1:1, v/v, acetic acid/water mixture. Compound 3 is subsequently purified by silica gel chromatography (eluent: cyclohexane/EtOAc, 6:4, v/v) to give a white powder with a yield of 40% from the 4-cyanobenzaldehyde.

Workup

  1. customthe dioxolane protecting group is removed by treatment in a 1:1, v/v, acetic acid/water mixture
  2. customCompound 3 is subsequently purified by silica gel chromatography (eluent: cyclohexane/EtOAc, 6:4, v/v)

Sources & evidence

ORD record
ord-06567bf4ccce44dfa8543fe72c56cd12
Source dataset
uspto-grants-2012_05
Patent number
US08173843B2

Reaction notes

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