Acetyl chloride → 3-(2-Hydroxy-1-methyl-ethylamino)-5-(1-methyl-hexa-1,3,5-trienyl)-thiophene-2-carboxylic acid methyl ester

HRID 73217Notes

Reaction equation

HRID 73217 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:8][C:9]=1[NH:10][CH:11]([CH3:21])[CH2:12][O:13][Si](C(C)(C)C)(C)C)=[O:4].[C:28](Cl)(=O)C>CO>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:22]([CH3:28])=[CH:27][CH:26]=[CH:25][CH:24]=[CH2:23])=[CH:8][C:9]=1[NH:10][CH:11]([CH3:21])[CH2:12][OH:13])=[O:4]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 59752395HCID 59752395, compound

Product 1

HCID 865958583-(2-Hydroxy-1-methyl-ethylamino)-5-(1-methyl-hexa-1,3,5-trienyl)-thiophene-2-carboxylic acid methyl esterYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 3-[2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethylamino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (1.08 g, 2.69 mmol) in MeOH (10 ml) at 21°, under N2 was added a solution of acetylchloride premixed in MeOH (100 μL/1 mL, 210 μL 2.96 mmol, 1.1 eq). The reaction was followed by tlc. On completion the reaction was stripped-off solvent and the residue purified over silica using progressively 5%, 20%, and then 30% EtOAc/Hexane as eluent to give 3-(2-Hydroxy-1-methyl-ethylamino)-5-(1-methyl-hexa-1,3,5-trienyl)-thiophene-2-carboxylic acid methyl ester as a yellow solid (518 mg, 79%); 1H NMR (300 MHz, CDCl3) 1.25 (d, 6.6 Hz, 3H), 3.52-3.62 (m, 1H), 3.73-3.77 (m, 2H), 3.84 (s, 3H), 6.92 (s, 1H), 7.36-7.42 (m, 3H), 3.62 (d, J=8.3 Hz, 2H).

Workup

  1. customthe residue purified over silica using progressively 5%, 20%

Sources & evidence

ORD record
ord-c08db65c25204b58b6b3e18f7cd05e7e
Source dataset
uspto-grants-2014_09
Patent number
US08829030B2

Reaction notes

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