Iodoethane → 3,5,5-Triethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid

HRID 2366112Notes

Reaction equation

HRID 2366112 reaction equation
[CH2:1]([C:3]1([CH2:15][CH3:16])[CH2:14][CH2:13][C:6]2=[C:7]([C:10]([OH:12])=[O:11])[S:8][CH:9]=[C:5]2[CH2:4]1)[CH3:2].[Li][CH2:18][CH2:19]CC.C(I)C>CC#N>[CH2:18]([C:9]1[S:8][C:7]([C:10]([OH:12])=[O:11])=[C:6]2[CH2:13][CH2:14][C:3]([CH2:1][CH3:2])([CH2:15][CH3:16])[CH2:4][C:5]=12)[CH3:19]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 575088915,5-Diethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acidHCID 178418339Butyllithium

Product 1

HCID 675203663,5,5-Triethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,5,5-Triethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid is prepared from 5,5-diethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid by treatment with tert.-BuLi followed by ethyliodide in analogy to Example C; LC-MS: tR=1.07 min, [M+1+CH3CN]=308.14.

Sources & evidence

ORD record
ord-59913589776d493b878ebc1298c17113
Source dataset
uspto-grants-2014_04
Patent number
US08697732B2

Reaction notes

Loading…