Lithium Hydroxide → HCID 59354898, compound

HRID 1099451Notes

Reaction equation

HRID 1099451 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[CH2:16][CH2:15][CH:14]1[CH2:17][OH:18].[OH-].[Li+]>>[O:13]1[CH2:16][CH2:15][CH:14]1[CH2:17][O:18][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 12284142(Oxetan-2-yl)methanol

Product 1

HCID 59354898HCID 59354898, compoundYield 42%

Conditions

Temperature
75 °C

Procedure

The title compound was synthesized as described for Intermediate example I-81 in 42% yield starting from ethyl 6-chloronicotinate and oxetan-2-ylmethanol. The reduction was performed using 3 equiv of lithium hydroxide while heating to 75° C. for 3.5 h. The final aqueous solution was extracted with ethyl acetate in order to collect the product; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.71 (d, 1 H), 8.16 (dd, 1 H), 6.96 (dd, 1 H), 4.96-5.06 (m, 1 H), 4.41-4.57 (m, 4 H), 2.64-2.75 (m, 1 H), 2.46-2.56 (m, 1 H); S (ESI) m/z 210[M+H+], m/z 208[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-11e1447d68b141689c9383891d5de242
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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