Phenol → HCID 573755, compound

HRID 2377253Notes

Reaction equation

HRID 2377253 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(N=C=NC2CCCCC2)CCCCC1.ClCCl.[S:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[C:31](O)=[O:32]>CN(C)C1C=CN=CC=1.C(OCC)C>[S:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[C:31]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:32]

Participants

7

Reactant 4

HCID 996PhenolHCID 6344DichloromethaneHCID 107002-Thiophenecarboxylic acidHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 573755HCID 573755, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

Phenol (5.0 g, 39.0 mmol), a 1M solution of 1,3-dicyclohexylcarbodiimide in dichloromethane (39.0 mL, 39.0 mmol) and 4-dimethylaminopyridine (0.5 g, 3.9 mmol) were added to a solution of thiophene-2-carboxylic acid (5.0 g, 39.0 mmol) in diethyl ether (400 mL) at about 0° C. The reaction mixture was stirred overnight while being allowed to warm to room temperature. The precipitate was collected by filtration and was washed with diethyl ether. The combined filtrates were washed successively with water, 5% aqueous acetic acid, water and brine, dried (MgSO4), filtered and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel using hexane/ethyl acetate (5:1) as the mobile phase to provide phenyl thiophene-2-carboxylate. MS (DCI-NH3): m/z 222 (M+NH4)+.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwas washed with diethyl ether
  3. washThe combined filtrates were washed successively with water, 5% aqueous acetic acid, water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-69543c198b5a47c8b7fcac17a2e7c8ed
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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