Hydrochloric Acid → 3-(Pent-2-en-3-yl)-2,2'-bitiophene

HRID 2193808Notes

Reaction equation

HRID 2193808 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6](O)([CH2:9][CH3:10])[CH2:7][CH3:8])=[C:2]1[C:12]1[S:13][CH:14]=[CH:15][CH:16]=1.Cl>C(O)(=O)C>[CH3:8][CH:7]=[C:6]([C:3]1[CH:4]=[CH:5][S:1][C:2]=1[C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 498402833-(2,2'-Bithiophene-3-yl)pentan-3-ol

Product 1

HCID 679963483-(Pent-2-en-3-yl)-2,2'-bitiophene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

3-(2,2′-bithiophene-3-yl)pentan-3-ol (IIa) (0.100 g, 0.40 mmol) was dissolved in acetic acid (69 mL). A solution of concentrated HCl (0.28 mL) in acetic acid (15 mL) was added via syringe to the reaction mixture. The solution was refluxed for 4 h followed by an extraction with chloroform, washing and drying over MgSO4. The solvent was removed in vacuo. The residue was purified by column chromatography on silica (n-Hexane). (0.070 g, 75%).

Workup

  1. temperatureThe solution was refluxed for 4 h
  2. extractionfollowed by an extraction with chloroform
  3. washwashing
  4. dry with materialdrying over MgSO4
  5. customThe solvent was removed in vacuo
  6. customThe residue was purified by column chromatography on silica (n-Hexane)

Sources & evidence

ORD record
ord-c408fb10b8f3415da4b6d5c154bfe0f1
Source dataset
uspto-grants-2012_12
Patent number
US08329923B2

Reaction notes

Loading…