Carbon Dioxide → Propiolic Acid

HRID 1379081

반응식

HRID 1379081 반응식
[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]

참가 물질

8

반응물 5

HCID 280Carbon Dioxide2회HCID 7864Chloromethyl Methyl EtherHCID 108454055-(Bromomethyl)-3-methoxy-1,2-oxazoleHCID 229062843-Diphenylmethoxy-4-iodomethyl-1,2,5-thiadiazoleHCID 178462446HCID 178462446, 화합물2회

생성물 2

HCID 10110Propiolic AcidHCID 178462446HCID 178462446, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  1. customthe like, to prepare the formula I compounds

출처 및 근거

ORD 기록
ord-0959af75a1d443efa21b0b9362963da6
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05670516

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