Lithium Hydroxide → 6-(1,4-Dioxan-2-ylmethoxy)-3-pyridinecarboxylic acid

HRID 1099452Notes

Reaction equation

HRID 1099452 reaction equation
Cl[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][N:3]=1.[O:13]1[CH2:18][CH2:17][O:16][CH2:15][CH:14]1[CH2:19][OH:20].[OH-].[Li+]>>[O:13]1[CH2:18][CH2:17][O:16][CH2:15][CH:14]1[CH2:19][O:20][C:2]1[CH:12]=[CH:11][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 2799611Ethyl 6-chloronicotinateHCID 12655091(1,4-Dioxan-2-yl)methanol

Product 1

HCID 593549026-(1,4-Dioxan-2-ylmethoxy)-3-pyridinecarboxylic acidYield 58%

Procedure

The title compound was synthesized as described for Intermediate example I-81 in 58% yield starting from ethyl 6-chloronicotinate and 1,4-dioxan-2-ylmethanol. The reduction was performed using 3 equiv of lithium hydroxide. The final aqueous solution was extracted with ethyl acetate in order to collect the product; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.70 (d, 1 H), 8.14 (dd, 1 H), 6.93 (d, 1 H), 4.28-4.32 (m, 2 H), 3.84-3.92 (m, 1 H), 3.72-3.83 (m, 2 H), 3.56-3.69 (m, 2 H), 3.44-3.55 (m, 1 H), 3.35-3.42 (m, 1 H); S (ESI) m/z 240[M+H+], m/z 238[M−H+];

Workup

  1. extractionThe final aqueous solution was extracted with ethyl acetate in order
  2. customto collect the product

Sources & evidence

ORD record
ord-82c4641221a54c60974ea6b9bba9c736
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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