Water → HCID 23130404, compound

HRID 2080089Notes

Reaction equation

HRID 2080089 reaction equation
C([Li])CCC.Br[C:7]1[S:11][C:10]([CH:12]2[O:16][CH2:15][CH2:14][O:13]2)=[CH:9][CH:8]=1.[CH3:17][C:18]1[S:22][C:21]([CH:23]=[O:24])=[CH:20][CH:19]=1.O>O1CCCC1.C(OCC)(=O)C>[O:13]1[CH2:14][CH2:15][O:16][CH:12]1[C:10]1[S:11][C:7]([CH:23]([C:21]2[S:22][C:18]([CH3:17])=[CH:19][CH:20]=2)[OH:24])=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 616635-Methyl-2-thiophenecarboxaldehydeHCID 122699702-(5-Bromothiophen-2-Yl)-1,3-DioxolaneHCID 178418339Butyllithium

Product 1

HCID 23130404HCID 23130404, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

n-Butyl lithium (2.44N hexane solution, 7.4 mL, 17.9 mmol) was added dropwise to a solution of 2-(5-bromo-thiophen-2-yl)-[1,3]dioxolane (4.0 g, 17 mmol) in tetrahydrofuran (50 mL) at from −75° C. to −70° C., and the solution was stirred for 10 minutes. 5-Methylthiophene-2-carbaldehyde (2.4 g, 18.7 mmol) was further added dropwise to the reaction solution at from −75° C. to −70° C. After dropwise addition was completed, the reaction solution was gradually allowed to room temperature. Water and ethyl acetate were added to the reaction mixture, which was then partitioned, and the solvent was evaporated. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=4:1, then 2:1), and the title compound (2.0 g, 7.09 mmol, 41.7%) was obtained as a brown oil.

Workup

  1. additionAfter dropwise addition
  2. customwas gradually allowed to room temperature
  3. customwas then partitioned
  4. customthe solvent was evaporated
  5. customThe residue was purified by NH silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-5c37ff543c4c4b3daa2d6f2e2587c7af
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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