5-Methyl-2-thiophenecarboxaldehyde → HCID 23577305, compound

HRID 1351597Notes

Reaction equation

HRID 1351597 reaction equation
C(OP([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(OCC)=O)C.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:27][C:28]1[S:32][C:31]([CH:33]=O)=[CH:30][CH:29]=1>C1COCC1>[CH3:33][C:31]1[S:32][C:28](/[CH:27]=[CH:9]/[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 616635-Methyl-2-thiophenecarboxaldehydeHCID 2733832Lithium HexamethyldisilazideHCID 2773685tert-Butyl diethylphosphonoacetate

Product 1

HCID 23577305HCID 23577305, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl diethylphosphonoacetate (1.12 mL, 4.76 mmol) in THF (5 mL) at −78° C. was added LHMDS (1.0M in THF, 4.76 mL, 4.76 mmol). After 5 min at −78° C. 5-methyl-2-thiophene-carboxaldehyde (0.43 mL, 3.96 mmol) was added. The reaction mixture was warmed to RT, stirred for 10 min and poured onto EtOAc/H2O. The layers were separated and the organic layer was washed with H2O, dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica (gradient elution; hexanes to 4:1 hexanes:EtOAc) to give tert-butyl (2E)-3-(5-methylthien-2-yl)prop-2-enoate as a clear oil.

Workup

  1. additionpoured onto EtOAc/H2O
  2. customThe layers were separated
  3. washthe organic layer was washed with H2O
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica (gradient elution; hexanes to 4:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-033a3a859b354f41ba1dcfc064ac80fe
Source dataset
uspto-grants-2007_05
Patent number
US07217716B2

Reaction notes

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