Acrylate → HCID 67551065, compound

HRID 1368989Notes

Reaction equation

HRID 1368989 reaction equation
[S:1]1[C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH:3]=[C:2]1[CH:9]=O.[CH2:11]([O:13][C:14](=[O:19])[CH2:15][N:16]=[N+]=[N-])[CH3:12].[O-]CC.[NH4+].[Cl-].C([O-])(=O)C=C>O.CCOCC.C(O)C>[CH2:11]([O:13][C:14]([C:15]1[NH:16][C:3]2[C:4]3[CH:8]=[CH:7][S:6][C:5]=3[S:1][C:2]=2[CH:9]=1)=[O:19])[CH3:12]

Participants

9

Reactant 5

HCID 25188Acrylate2×HCID 25517Ammonium ChlorideHCID 69480Acetic acid, azido-, ethyl esterHCID 1194401-Hydroxyethyl radicalHCID 3567708Thieno[2,3-b]thiophene-2-carboxaldehyde

Product 1

HCID 67551065HCID 67551065, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Thieno[2,3-b]thiophene-2-carbaldehyde (Dopper, J. H. et al., J. Am. Chem. Soc., 95: 3692-8 (1973)) was annulated according to Procedure H (aldehyde and azido-acetic acid ethyl ester added as ethanol solution (1 M of ester) to −20° C. ethoxide solution; −20° C. 30 min, −20° C. to room temperature over 2.5 h; reaction poured into cold saturated aqueous NH4Cl; after ether extraction, acrylate organic phase washed with water until aqueous phase was neutral; 0.35 M solution of crude acrylate heated).

Sources & evidence

ORD record
ord-049ea432ecc247a2bf2c9a5c3d6157ea
Source dataset
uspto-grants-2003_06
Patent number
US06576653B2

Reaction notes

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