Tetrahydrofuran → 5-Ethoxycarbonylamino-2-(3,3,3-trifluoropropyl)-benzofuran

HRID 582620Notes

Reaction equation

HRID 582620 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][CH2:11][C:12]([F:15])([F:14])[F:13])=[CH:7][C:6]=2[CH:16]=1.O1CCCC1.Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])O.[Na+]>O.ClCCl>[CH2:26]([O:25][C:23]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][CH2:11][C:12]([F:15])([F:13])[F:14])=[CH:7][C:6]=2[CH:16]=1)=[O:24])[CH3:27]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 221329575-Amino-2-(3,3,3-trifluoropropyl)benzofuran

Product 1

HCID 111303975-Ethoxycarbonylamino-2-(3,3,3-trifluoropropyl)-benzofuranYield 95.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.0 g (8.7 mmol) of 5-amino-2-(3,3,3-trifluoropropyl)benzofuran in 30 ml of a 9/1 mixture of tetrahydrofuran and water is reacted for 30 minutes with 0.92 ml (9.6 mmol) of ethyl chloroformate in the presence of 1.1 g (13 mmol) of sodium hydrogen-carbonate. The reaction medium is then diluted with water and dichloromethane, then the organic phase is separated, dried over sodium sulfate and concentrated under reduced pressure. 2.5 g of product are obtained.

Workup

  1. customthe organic phase is separated
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0b99d8c12dd8436aa44b9524aeacef89
Source dataset
uspto-grants-1999_07
Patent number
US05925662

Reaction notes

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