2-(2-Hydroxyethyl)pyridine → 2-Methyl-6-[3-(2-pyridin-2-yl-ethoxy)-phenoxymethyl]-phenoxy-acetonitrile

HRID 892148Notes

Reaction equation

HRID 892148 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)[C:3]=1[O:4][CH2:5][C:6]#[N:7].[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][CH2:28]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:28][CH2:27][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=3)[CH:15]=2)[C:3]=1[O:4][CH2:5][C:6]#[N:7]

Participants

6

Reactant 4

HCID 76752-(2-Hydroxyethyl)pyridineHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 22241289(2-[3-Hydroxyphenoxymethyl]-6-methylphenoxy)acetonitrile

Product 1

HCID 222414332-Methyl-6-[3-(2-pyridin-2-yl-ethoxy)-phenoxymethyl]-phenoxy-acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [2-methyl-6-(3-hydroxy-phenoxymethyl)-phenoxy]-acetonitrile (135 mg, 0.5 mmol, example 25) and 2-(pyridin-2-yl)-ethanol (126 mL, 0.94 mmol) in THF (2 mL) is added triphenylphosphine (262 mg, 1 mmol) followed by DEAD (118 mL, 0.75 mmol). The resulting solution is stirred for 2 h, then concentrated and the residue purified by flash chromatography (silica, 50% ethyl acetate in hexanes) to give the title compound as an oil. MS (ESI) 375 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customthe residue purified by flash chromatography (silica, 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5b33e6ffe26c4b47996a382134f572ee
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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