Ethyl 2-thienylacetate → 8-(5-Methyl-2-phenyl-oxazol-4-yl)-2-thiophen-2-yl-oct-4-ynoic acid ethyl ester

HRID 2121700Notes

Reaction equation

HRID 2121700 reaction equation
COC(=O)C(N1C=CC=C1)[CH2:5][C:6]#[C:7][CH2:8][CH2:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:14][C:15]=1[CH3:16].[CH3:29][CH2:30][O:31][C:32]([CH2:34][C:35]1[S:39][CH:38]=[CH:37][CH:36]=1)=[O:33]>>[CH2:30]([O:31][C:32](=[O:33])[CH:34]([C:35]1[S:39][CH:38]=[CH:37][CH:36]=1)[CH2:5][C:6]#[C:7][CH2:8][CH2:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[O:14][C:15]=1[CH3:16])[CH3:29]

Participants

3

Reactant 2

HCID 93657Ethyl 2-thienylacetateHCID 120932718-(5-Methyl-2-phenyl-oxazol-4-yl)-2-pyrrol-1-yl-oct-4-ynoic acid methyl ester

Product 1

HCID 120932738-(5-Methyl-2-phenyl-oxazol-4-yl)-2-thiophen-2-yl-oct-4-ynoic acid ethyl esterYield 38%

Procedure

Prepared in a manner similar to ester 1-10 with the exception that Ethyl 2-thiophene acetate was used instead of Methyl 2-pyrrolo-acetate. Chromatography gave 206 mg of the ethyl ester 1-12 (38% yield) as a yellow oil. NMR CDCl3 (δ): 7.99 (2H, m); 7.43 (3H, m); 7.21 (1H, dd, J=1.0, 5.1 Hz); 6.98 (1H, m); 6.94 (1H, m); 4.22 (2H, m); 4.03 (1H, t, J=7.0, 8.0 Hz), 2.92 (1H, m); 2.71 (1H, m); 2.54 (2H, t, J=7.3, 7.3 Hz); 2.31 (3H, s); 2.14 (2H, m); 1.81 (2H, m); 1.25 (3H, t, J=7.1, 7.1 Hz). M+1=408.2.

Sources & evidence

ORD record
ord-1b3657940c1847e898dd9aa40c736620
Source dataset
uspto-grants-2004_02
Patent number
US06696474B2

Reaction notes

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