3-Hydroxypyridine → HCID 14986715, compound

HRID 465613Notes

Reaction equation

HRID 465613 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1.[C:27]([CH2:29][CH2:30][CH:31](O)[CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])#[N:28].N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl.CCOCC>[C:27]([CH2:29][CH2:30][CH:31]([O:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])#[N:28]

Participants

7

Reactant 4

HCID 79713-HydroxypyridineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 14986714HCID 14986714, compound

Product 1

HCID 14986715HCID 14986715, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of triphenylphosphine (2.42 g, 9.2 mmol) and 3-hydroxypyridine (0.7 g, 7.3 mmol) in methylene chloride (20 ml) is added the ethyl 7-cyano-5-hydroxyheptanoate obtained above. The reaction mixture is stirred for 5 min and then diethyl azodicarboxylate (1.0 ml, 6.3 mmol) is added dropwise. The reaction mixture is stirred overnight and the solvent is evaporated. The residue is chromatographed on silica gel using ether as eluent to obtain an amber oil. The oil is dissolved in 10 ml ether, cooled to 0° and the precipitated triphenylphosphine oxide is filtered off. The filtrate is evaporated to give crude ethyl 7-cyano-5-(3-pyridyloxy)-heptanoate, IR (CH2Cl2): 2239, 1729, 1576, 1229, 1167, 1120 cm-1.

Workup

  1. customobtained above
  2. stirringThe reaction mixture is stirred overnight
  3. customthe solvent is evaporated
  4. customThe residue is chromatographed on silica gel
  5. customto obtain an amber oil
  6. temperaturecooled to 0°
  7. filtrationthe precipitated triphenylphosphine oxide is filtered off
  8. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-582cd08684914b1291fce7752d219652
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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