2-(Trimethylsilyl)ethanol → 5-Methyl-thiophene-2-carboxylic acid 2-trimethylsilanylethyl ester

HRID 1591992Notes

Reaction equation

HRID 1591992 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.Cl.[CH3:22][Si:23]([CH3:28])([CH3:27])[CH2:24][CH2:25]O>CC#N.CN(C1C=CN=CC=1)C>[CH3:22][Si:23]([CH3:28])([CH3:27])[CH2:24][CH2:25][O:8][C:7]([C:5]1[S:6][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:9]

Participants

6

Reactant 3

HCID 180132-(Trimethylsilyl)ethanolHCID 747135-Methylthiophene-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 671384295-Methyl-thiophene-2-carboxylic acid 2-trimethylsilanylethyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of 5-Methyl-thiophene-2-carboxylic acid (23.58 g, 166 mmol) in MeCN (300 mL) is treated with EDCl (33.41 g, 174 mmol) and DMAP (2.03 g, 16 mmol). The mixture is stirred for 5 min and 2-(trimethylsilyl)ethanol (19.61 g, 166 mmol) is added. The mixture is stirred at RT for 16 h and the solvent is evaporated. The residue is partitioned between EtOAc and water. The organic layer is diluted with an equal portion of hexane and dried over anhydrous MgSO4. The solution is passed through a plug of silica gel and the solvents are evaporated to dryness to give 5-methyl-thiophene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester as a clear oil.

Workup

  1. stirringThe mixture is stirred at RT for 16 h
  2. customthe solvent is evaporated
  3. customThe residue is partitioned between EtOAc and water
  4. additionThe organic layer is diluted with an equal portion of hexane
  5. dry with materialdried over anhydrous MgSO4
  6. customthe solvents are evaporated to dryness

Sources & evidence

ORD record
ord-d275e104edc94cbeaab43948cdae0950
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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