Carbon Dioxide → Propiolic Acid

HRID 1683326

反応式

HRID 1683326 の反応式
[C-]#[C-].[Li+:3].[Li+].C[O:6]CCl.BrC[C:11]1ON=[C:13]([O:16]C)[CH:12]=1.[C:18]1(C(C2C=CC=CC=2)OC2C(CI)=NSN=2)C=CC=C[CH:19]=1.C(=O)=O>O1CCCC1>[C:13]([OH:16])(=[O:6])[C:12]#[CH:11].[C-:18]#[C-:19].[Li+:3].[Li+:3]

参加物

8

反応物 5

HCID 280Carbon Dioxide2 回HCID 7864Chloromethyl Methyl EtherHCID 108454055-(Bromomethyl)-3-methoxy-1,2-oxazoleHCID 229062843-Diphenylmethoxy-4-iodomethyl-1,2,5-thiadiazoleHCID 178462446HCID 178462446、化合物2 回

生成物 2

HCID 10110Propiolic AcidHCID 178462446HCID 178462446、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Dibromoolefin intermediate XIX is then converted to ethynyl intermediate XX. Treatment of the dibromoolefin intermediate with about two equivalents of n-butyllithium produces the lithium acetylide XX, wherein R13 is Li. This transformation is typically carried out in a polar organic solvent, such as tetrahydrofuran, at a temperature of about -78° C. to about 25° C. The lithium acetylide is reacted with electrophiles, such as methoxymethyl chloride, 5-bromomethyl-3-methoxyisoxazole, 3-diphenylmethoxy-4-iodomethyl-1,2,5-thiadiazole, carbon dioxide, tetrazole disulfide, and the like, to prepare the formula I compounds. In a typical example, the lithium acetylide is treated with solid CO2 at a temperature of about -78° C. to about -60° C. to produce propargylic acid intermediate XX wherein R13 is CO2H. This compound may be further modified as described herein.

後処理

  1. customthe like, to prepare the formula I compounds

出典と根拠

ORDレコード
ord-ada062d1d2374f2db691a9c07b9eaf1b
出典データセット
uspto-grants-1997_06
特許番号
US05637712

関連ノート

読み込み中…