Diethyl Oxalate → 4,5-Dihydro-5,8-dimethyl-4-oxopyrano[3,2-b]indole-2-carboxylic acid

HRID 46731

반응식

HRID 46731 반응식
[CH3:1][C:2]([C:4]1[N:5]([CH3:15])[C:6]2[C:11]([C:12]=1[OH:13])=[CH:10][C:9]([CH3:14])=[CH:8][CH:7]=2)=[O:3].[Na].[C:17](OCC)(=O)[C:18]([O:20]CC)=[O:19].[Na][Na]>C(O)C>[CH3:15][N:5]1[C:6]2[CH:7]=[CH:8][C:9]([CH3:14])=[CH:10][C:11]=2[C:12]2[O:13][C:17]([C:18]([OH:20])=[O:19])=[CH:1][C:2](=[O:3])[C:4]1=2

참가 물질

6

반응물 4

HCID 7268Diethyl OxalateHCID 141233DisodiumHCID 5360545SodiumHCID 125113281,5-dimethyl-3-hydroxy-1H-indol-2-yl methyl ketone

생성물 1

HCID 126284314,5-Dihydro-5,8-dimethyl-4-oxopyrano[3,2-b]indole-2-carboxylic acid

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

In a manner analogous to that of Example 14, 8.2 g (0.040 mole) of 1,5-dimethyl-3-hydroxy-1H-indol-2-yl methyl ketone (Example 12) was reacted with sodium metal (3.7 g, 0.16 mole) and diethyl oxalate (21.5g, 0.20 mole) in 200 ml absolute ethanol. The red disodium salt intermediate was then converted to the title compound as described in Example 17. Two recrystallization of the final product from DMF-water yielded yellow needles of mpt. 290°.

출처 및 근거

ORD 기록
ord-9977afb92eca43458dada9068c15f795
출처 데이터셋
uspto-grants-1979_11
특허 번호
US04175083

연결된 노트

불러오는 중…