Methyl iodide → 5,5-Diethyl-3-methyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid

HRID 1924816Notes

Reaction equation

HRID 1924816 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]CCC.CI>CC#N>[CH2:15]([C:3]1([CH2:1][CH3:2])[CH2:14][CH2:13][C:6]2=[C:7]([C:10]([OH:12])=[O:11])[S:8][C:9]([CH3:18])=[C:5]2[CH2:4]1)[CH3:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 575088915,5-Diethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acidHCID 178418339Butyllithium

Product 1

HCID 675203685,5-Diethyl-3-methyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5,5-Diethyl-3-methyl-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 methyliodide in analogy to Example C; LC-MS: tR=1.03 min, [M+1+CH3CN]=294.27.

Sources & evidence

ORD record
ord-be553fbb789641f38f249a5e54e85647
Source dataset
uspto-grants-2012_05
Patent number
US08178562B2

Reaction notes

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