3-Hydroxypyridine → HCID 14986715, compound

HRID 1494152Notes

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

Conditions

Temperature: 0 °C

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 minutes 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° C. 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

customobtained above
stirringThe reaction mixture is stirred overnight
customthe solvent is evaporated
customThe residue is chromatographed on silica gel
customto obtain an amber oil
filtrationthe precipitated triphenylphosphine oxide is filtered off
customThe filtrate is evaporated

Sources & evidence

ORD record: ord-c99cfbea2f594d11a4b2787d8e7860a8
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05025025

Reaction notes

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