Benzoic Acid → cyano-(2,3-dihydro-5-methoxy-2-methyl-1H-inden-1-ylidene)acetic acid 2-ethyl-hexyl ester

반응식

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH:7]([CH3:13])[CH2:6]2.[NH:14]1C[CH2:17][CH2:16][CH2:15]1.[C:19](O)(=[O:26])C1C=CC=CC=1.[OH2:28].[C:29]1([CH3:35])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH2:29]([CH:34]([CH2:33][CH2:32][CH2:31][CH3:30])[CH2:19][O:26][C:17](=[O:28])[C:16]([C:15]#[N:14])=[C:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[CH2:6][CH:7]1[CH3:13])[CH3:35]

참가 물질

반응물 5

HCID 243Benzoic Acid

HCID 962Water

HCID 1140Toluene

HCID 31268Pyrrolidine

HCID 122904905-Methoxy-2-methylindan-1-one

생성물 1

HCID 69822365cyano-(2,3-dihydro-5-methoxy-2-methyl-1H-inden-1-ylidene)acetic acid 2-ethyl-hexyl ester

실험 절차

The above 2,3-dihydro-5-methoxy-2-methyl-1H-inden-1-one (5.2 g) was reacted with 5.9 g of 2-ethyl-hexyl cyano acetate in the presence of catalytic amounts of pyrrolidine and benzoic acid in 100 ml of toluene. The reaction mixture was refluxed for 30 hours with simultaneous separation of water. Then, the cold reaction mixture was washed with water, concentrated and chromatographed in toluene containing 2% of propanol through SiO2 to yield 2.6 g of a yellow liquid. UV 347 nm (ε=33′450), MS: 355(M+), 243 (100%), 226, 198.