Water → HCID 67119582, compound

HRID 2080138Notes

Reaction equation

HRID 2080138 reaction equation
[CH3:1][C:2]([CH3:5])([O-])C.[K+].[Cl-].[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH2:13][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.[CH3:34]N(C)C=O>>[CH:5]1([CH:34]=[CH:13][C:9]2[S:8][CH:12]=[CH:11][CH:10]=2)[CH2:2][CH2:1]1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 115747672-Thienylmethyltriphenylphosphonium chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 67119582HCID 67119582, compoundYield 52.3%

Procedure

Potassium tert-butoxide (1.81 g, 16.2 mmol) was suspended in N,N-dimethylformamide (50 mL), thiophen-2-ylmethyl triphenylphosphonium chloride (6.38 g, 16.2 mmol) was added while stirring at room temperature under a nitrogen stream, and the mixture was stirred at room temperature for 30 minutes. Then, cyclopropanecarboxyaldehyde (1.13 g, 16.2 mmol) was added dropwise to the reaction solution, and the solution was stirred for 1 hour. Water (100 mL) was added to the reaction solution, which was then extracted with hexane (50 mL). The organic layer was passed through silica gel (10 g) for filtration, the filtrate was evaporated in vacuo, and the title compound (1.27 g, 8.47 mmol, 52.3%) was obtained as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. additionThen, cyclopropanecarboxyaldehyde (1.13 g, 16.2 mmol) was added dropwise to the reaction solution
  3. stirringthe solution was stirred for 1 hour
  4. extractionwas then extracted with hexane (50 mL)
  5. filtrationThe organic layer was passed through silica gel (10 g) for filtration
  6. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-1e430fba91bd4f1495e100d970801c52
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

Loading…