Water → HCID 67387443, compound

HRID 910700Notes

Reaction equation

HRID 910700 reaction equation
[Li][CH2:2]CCC.[Cl:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([C:13]2[CH:14]=[C:15]([CH:18]=O)[S:16][CH:17]=2)[CH:8]=1.O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Cl:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([C:13]2[CH:14]=[C:15]([CH:18]=[CH2:2])[S:16][CH:17]=2)[CH:8]=1

Participants

6

Reactant 3

HCID 962WaterHCID 86628638HCID 86628638, compoundHCID 178418339Butyllithium

Product 1

HCID 67387443HCID 67387443, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyltriphenylphosphonium bromide (180 mg, 0.5 mmol) in THF (3 mL) was added n-BuLi (1.6 M, 0.34 mL) at 0° C. After the mixture was stirred for 30 minutes, a solution of 4-(4-chloro-pyridin-2-yl)-thiophene-2-carbaldehyde (100 mg, 0.45 mmol) in THF (2 mL) was added. The resulting mixture was stirred at room temperature for 5 hours. Water was added and THF was removed. The water solution was extracted with EtOAc and organic layer was concentrated. The resulting residue was purified by silica gel column to yield 4-chloro-2-(5-vinyl-thiophen-3-yl)-pyridine.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 5 hours
  2. customTHF was removed
  3. extractionThe water solution was extracted with EtOAc and organic layer
  4. concentrationwas concentrated
  5. customThe resulting residue was purified by silica gel column

Sources & evidence

ORD record
ord-aca901be3de8469caae63d71e0282d27
Source dataset
uspto-grants-2011_09
Patent number
US08022209B2

Reaction notes

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