1,8-Diazabicyclo(5.4.0)undec-7-ene → Thiophene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester

HRID 1591994Notes

Reaction equation

HRID 1591994 reaction equation
COC1C=C(OC)C=CC=1CN1C(=O)CNS1(=O)=O.C1CCN2C(=NCCC2)CC1.[CH3:31][Si:32]([CH3:46])([CH3:45])[CH2:33][CH2:34][O:35][C:36]([C:38]1[S:39][C:40](CBr)=[CH:41][CH:42]=1)=[O:37]>C(Cl)Cl>[CH3:31][Si:32]([CH3:46])([CH3:45])[CH2:33][CH2:34][O:35][C:36]([C:38]1[S:39][CH:40]=[CH:41][CH:42]=1)=[O:37]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 66751042HCID 66751042, compoundHCID 67138806HCID 67138806, compound

Product 1

HCID 86591038Thiophene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the title B compound in Example 9, 2-(2,4-dimethoxybenzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (7.00 g, 24.4 mmol) and DBU (3.71 g, 24.4 mmol) in CH2Cl2 (200 mL) is treated with the title B compound, 5-bromomethyl-thiophene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester (8.25 g, 25.7 mmol). The mixture is stirred at RT for 3 h and the solvent is evaporated. The residue is chromatographed over silica gel using 20%-50% EtOAc in hexane as the eluent to afford 5-[5-(2,4-dimethoxy-benzyl)-1,1,4-trioxo-1,2,5]thiadiazolidin-2-ylmethyl]-thiophene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester as a yellow oil.

Workup

  1. customthe solvent is evaporated
  2. customThe residue is chromatographed over silica gel using 20%-50% EtOAc in hexane as the eluent

Sources & evidence

ORD record
ord-7fefd366b0d84979a2237efd63dec5d3
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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