Tetrahydrofuran → HCID 86679331, compound

HRID 529873Notes

Reaction equation

HRID 529873 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH:15]=[C:14](Br)[S:13][C:12]=1Br.C([Li])CCC.[CH:23](N1CCCCC1)=[O:24].C1C[O:34][CH2:33]C1>CCCCCC>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH:15]=[C:14]([CH:33]=[O:34])[S:13][C:12]=1[CH:23]=[O:24]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 174291-PiperidinecarboxaldehydeHCID 86679332HCID 86679332, compoundHCID 178418339Butyllithium

Product 1

HCID 86679331HCID 86679331, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

See Reaction Scheme 434 in FIG. 4E. A solution of 0.01 mole of 3-naphth-2-yl-2,5-dibromothiophene (prepared as described in Example 10) may be prepared in about 10 milliliters of anhydrous THF and cooled using a dry ice/acetone bath under an inert atmosphere. About 0.021 mole of n-butyllithium in hexane may be added, and the mixture may be stirred for about 30 minutes. Next, about 0.021 mole of 1-formyl piperidine may be added, and the mixture may be stirred and allowed to rise to room temperature over about 12 hours. The reaction mixture may be washed with aqueous ammonium chloride, and the organic layer may be dried and evaporated to form a residue. The residue may be purified via silica gel chromatography to give 3-(naphthalen-2-yl)thiophene-2,5-dicarbaldehyde.

Workup

  1. customReaction Scheme 434 in FIG. 4E
  2. temperaturecooled
  3. stirringthe mixture may be stirred
  4. waitto rise to room temperature over about 12 hours
  5. washThe reaction mixture may be washed with aqueous ammonium chloride
  6. customthe organic layer may be dried
  7. customevaporated
  8. customto form a residue
  9. customThe residue may be purified via silica gel chromatography

Sources & evidence

ORD record
ord-e868ab2b9b3f4126a8fe7beee0052f97
Source dataset
uspto-grants-2016_05
Patent number
US09350012B2

Reaction notes

Loading…