Ethyl Acetate → HCID 68690094, compound

HRID 1444993Notes

Reaction equation

HRID 1444993 reaction equation
[Li][CH2:2]CCC.[CH:6]([C:8]1[S:9][CH:10]=[C:11]([CH3:14])[C:12]=1[CH3:13])=O.CCOC(C)=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC.CCCCCC>[CH:6]([C:8]1[S:9][CH:10]=[C:11]([CH3:14])[C:12]=1[CH3:13])=[CH2:2]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 125183953,4-Dimethylthiophene-2-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 68690094HCID 68690094, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent2×

Procedure

To a solution of methyltriphenylphosphonium bromide (714 mg, 2 mmol) in ether at 0° C. was added dropwise 1.6 M n-BuLi solution in hexane (1.25 mL, 2.00 mmol). The resultant solution was stirred at 0° C. for 40 min and then was warmed to room temperature. A solution of 2-formyl-3,4-dimethylthiophene trimer (432 mg, 1.2 mol) was added slowly and the mixture was stirred overnight. The reaction mixture was quenched with ammonium chloride solution and diluted with ether. The organic phase was washed with water and brine, and dried with MgSO4. The ether was removed in vacuo to afford the crude product as an oil (260 mg). Column chromatography (2% EtOAc in hexane) afforded the purified 2-vinyl-3,4-dimethylthiophene trimer (140 mg, 37% yield). EI-MS: 358 (M+). 1H NMR (CDCl3) δ 6.98 (s, 1H), 6.90 (dd, 1H), 5.52 (d, 1H), 1.15 (d, 1H), 2.22 (s, 1H), 2.19 (s, 1H), 2.11 (s, 1H), 2.10 (s, 1H), 2.09 (s, 1H), 2.08 (s, 1H).

Workup

  1. customThe reaction mixture was quenched with ammonium chloride solution
  2. additiondiluted with ether
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried with MgSO4
  5. customThe ether was removed in vacuo
  6. customto afford the crude product as an oil (260 mg)

Sources & evidence

ORD record
ord-63108337cd924518818ae059606b51d0
Source dataset
uspto-grants-2010_02
Patent number
US07663301B2

Reaction notes

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