Methanol → Methyl 2-(5-((tert-butyldimethylsilyloxy)methyl)thiophen-2-yl)acetate

HRID 1020116Notes

Reaction equation

HRID 1020116 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[S:14][C:13]([CH2:15][C:16]([OH:18])=[O:17])=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:19]O>>[Si:1]([O:8][CH2:9][C:10]1[S:14][C:13]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 887MethanolHCID 595637742-(5-((Tert-butyldimethylsilyloxy)methyl)thiophen-2-yl)acetic acid

Product 1

HCID 59563701Methyl 2-(5-((tert-butyldimethylsilyloxy)methyl)thiophen-2-yl)acetate

Procedure

To 2-(5-((tert-butyldimethylsilyloxy)methyl)thiophen-2-yl)acetic acid (E231) in MeOH at 0° C. was added TMS-CH2N2 until the solution persisted in a yellow color and TLC indicated completion of the reaction. The solution stirred for 30 min and then was quenched with a few drops of AcOH. The solvents were evaporated and column chromatography (SiO2, 0-15% EtOAc/Hexanes) gave pure methyl 2-(5-((tert-butyldimethylsilyloxy)methyl)thiophen-2-yl)acetate (E232).

Workup

  1. customcompletion of the reaction
  2. customwas quenched with a few drops of AcOH
  3. customThe solvents were evaporated

Sources & evidence

ORD record
ord-c1da7b84339e4b1bbaafe82b375b3af0
Source dataset
uspto-grants-2014_05
Patent number
US08716310B2

Reaction notes

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