Benzyl lactate → HCID 19768414, compound

HRID 1590851

Reaction equation

HRID 1590851 reaction equation
[C:1](OCC1C=CC=CC=1)(=O)[CH:2]([CH3:4])O.[N:14](C(OCC)=O)=NC(OCC)=O.[CH2:26]([O:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[CH:46]=[CH:45][C:44]([OH:47])=[CH:43][N:42]=2)=[C:37]([F:48])[CH:36]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>>[CH2:26]([O:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[CH:46]=[CH:45][C:44]([O:47][CH:2]([C:1]#[N:14])[CH3:4])=[CH:43][N:42]=2)=[C:37]([F:48])[CH:36]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

4

Reactant 3

HCID 98054Benzyl lactateHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22717460HCID 22717460, compound

Product 1

HCID 19768414HCID 19768414, compound

Procedure

Optically active benzyl lactate is etherified by means of diethyl azodicarboxylate (DEAD)/triphenylphosphine with 2-(4-octyloxy-2-fluorophenyl)-5-hydroxypyridine (prepared in accordance with Example 1) and the benzyl group is then split off hydrogenolytically. The acid so obtained is converted as usual into the nitrile (oxalyl chloride, ammonia, thionyl chloride). Optically active 2-(4-octyloxy-2-fluorophenyl)-5-(1-cyanoethoxy)-pyridine is obtained.

Workup

  1. customthe benzyl group is then split off hydrogenolytically
  2. customThe acid so obtained

Sources & evidence

ORD record
ord-c13875652fd042b99e09cb22bf04964e
Source dataset
uspto-grants-1993_04
Patent number
US05204476

Linked notes

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