Carbon Dioxide → HCID 51064101, compound

HRID 566620Notes

Reaction equation

HRID 566620 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][C@H:7]([CH3:11])[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[K].C(=O)([O-])[O-].[K+].[K+].C(=O)=O.[Cl:24][C:25]1[CH:26]=[C:27]([F:32])[C:28](F)=[N:29][CH:30]=1.S(O[CH2:38][C:39]#[CH:40])(=O)(=O)C>C(#N)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:38]([O:9][C:8](=[O:10])[C@H:7]([O:6][C:5]1[CH:4]=[CH:3][C:2]([O:1][C:28]2[C:27]([F:32])=[CH:26][C:25]([Cl:24])=[CH:30][N:29]=2)=[CH:13][CH:12]=1)[CH3:11])#[C:39][CH3:40]

Participants

10

Reactant 6

HCID 280Carbon DioxideHCID 11430Potassium Carbonate2×HCID 179741(R)-2-(4-Hydroxyphenoxy)propionic acidHCID 305925propargyl mesylateHCID 27832485-Chloro-2,3-difluoropyridineHCID 5462222Potassium

Product 1

HCID 51064101HCID 51064101, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

182 g of (R)-2-(p-hydroxyphenoxy)-propionic acid 100% (1 mol) in 1500 g of acetonitrile are converted into the corresponding potassium salt by adding 69 g of potassium carbonate powder (0.5 mols) at 70°C. whilst cleaving the CO2. Then, 193 g of potassium carbonate powder (1.4 mols) and 2 g of tetrabutyl ammonium bromide as the phase transfer catalyst are added to the reaction mixture, and at a temperature of 70 to 75° C., 165 g of 5-chloro-2,3-difluoropyridine (1.1 mols) are added over the course of 30 minutes. After 8 hours, the compound of formula V thus obtained is reacted totally, by measuring in 154 g of propargyl mesylate (1.15 mols) as a 60-70% toluene solution over the course of 2 hours, directly, without isolation, at a temperature of 70-75° C., to form the (R)(+)-2-[4-(5-chloro-3-fluoropyridin-2-yloxy)-phenoxy]-propionic acid propinyl ester. Working up is effected analogously to example P1. 304 g of (R)(+)-2-[4-(5-chloro-3-fluoropyridin-2-yloxy)-phenoxy]-propionic acid propinyl ester are obtained with a content of 98% (GC), corresponding to a yield of 85% of theory, based on (R)-2-(p-hydroxyphenoxy)-propionic acid.

Workup

  1. customthe compound of formula V thus obtained
  2. customis reacted totally

Sources & evidence

ORD record
ord-9e387122fa614b55b9b02fd1649439be
Source dataset
uspto-grants-2001_01
Patent number
US06175018B1

Reaction notes

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