2-Thiophenecarboxylic acid → HCID 86679604, compound

HRID 1776657Notes

Reaction equation

HRID 1776657 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=[O:7].C([O-])([O-])=O.[K+].[K+].Br[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>CC(C)=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:7]

Participants

5

Reactant 3

HCID 107002-Thiophenecarboxylic acidHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 86679604HCID 86679604, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of thiophene-2-carboxylic acid (500 mg, 3.90 mmol) in acetone (20 ml), K2CO3 (593 mg, 4.29 mmol) was added, and mixture was stirred for 5 minutes, then KI (64.8 mg, 0.390 mmol) was added, followed by dropwise addition of tert-butyl 2-bromoacetate (0.634 ml, 4.29 mmol). The mixture was heated at 50° C. overnight. The solid residue was filtered out and washed with DCM; the solvent was evaporated and 2-tert-butoxy-2-oxoethyl thiophene-2-carboxylate was obtained as a clear oil (945 mg, 3.90 mmol, 100% yield, MS/ESI+ 264.9 [MNa]+) and used in the following reaction without further purification.

Workup

  1. additionKI (64.8 mg, 0.390 mmol) was added
  2. filtrationThe solid residue was filtered out
  3. washwashed with DCM
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-84e45c5ea85d4c33838dc4bdd875b744
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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