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Formic Acid → 5-Formyl-3-tert-butyl-thiophene-2-carboxylic acid methyl ester

HRID 1952564
Notes
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Reaction equation

HRID 1952564 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:14](OCC)[O:15]CC)=[CH:8][C:9]=1[C:10]([CH3:13])([CH3:12])[CH3:11])=[O:4].C(O)=O>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:14]=[O:15])=[CH:8][C:9]=1[C:10]([CH3:11])([CH3:12])[CH3:13])=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 284Formic AcidHCID 682265355-Diethoxymethyl-3-tert-butyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 866712585-Formyl-3-tert-butyl-thiophene-2-carboxylic acid methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-diethoxymethyl-3-tert-butyl-thiophene-2-carboxylic acid methyl ester (1.84 g, 6.1 mmol) in dioxane (10 ml) was cooled to 0° C. (ice bath). 88% formic acid (20 ml) was added in one portion and the mixture was stirred at 0° C. for 5 min and then at rt for 2 h. The mixture was concentrated under reduced pressure to afford the desired product which was not further purified (1.57 g, 100% yield).

Workup

  1. waitat rt for 2 h
  2. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-70e9845c2fa846cd9b426d517881a5ba
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08404859B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes