Ammonium Chloride → HCID 20060174, compound

HRID 1085487Notes

Reaction equation

HRID 1085487 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)=[O:6].[Cl-].[NH4+]>O1CCCC1>[CH3:2][C:3]1[CH:5]=[CH:7][S:8][C:4]=1[C:5]1([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)[CH2:4][CH2:3][CH2:2][O:6]1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 1235114-Chloro-1-(2-thienyl)butan-1-one

Product 1

HCID 20060174HCID 20060174, compoundYield 138.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction mixture was kept under reflux for 1 h after the exotherm had subsided and cooled to ambient temperature. To the reaction mixture was added 27.85 g of 4-chloro-1-(2-thienyl)-butan-1-on in 75 ml of anhydrous tetrahydrofuran. The reaction mixture was heated at reflux for 0.5 h, cooled and 175 ml of saturated ammonium chloride solution was introduced, and the mixture was extracted with 3×200 ml of ethyl acetate. The combined extracts were dried (MgSO4) and evaporated to an oil. Flash chromatography on silica gel (Art. 9385) eluting with heptane/ethyl acetate (40:1) provided 2-(3-methylthien-2-yl)-2-(thien-2-yl)tetrahydrofuran (25.58 g, 69%) as an oil.

Workup

  1. temperatureunder reflux for 1 h after the exotherm
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 0.5 h
  4. temperaturecooled
  5. extractionthe mixture was extracted with 3×200 ml of ethyl acetate
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. customevaporated to an oil
  8. washFlash chromatography on silica gel (Art. 9385) eluting with heptane/ethyl acetate (40:1)

Sources & evidence

ORD record
ord-41a92ffad6cc47cfabfd43e2e9a3dd0e
Source dataset
uspto-grants-1991_04
Patent number
US05010090

Reaction notes

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