Phosphonium → HCID 90456012, compound

HRID 588909Notes

Reaction equation

HRID 588909 reaction equation
[PH4+].[CH3:2]C([O-])(C)C.[K+].[Cl:8][C:9]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:10]=1[CH:11]=O>C1COCC1.C([O-])(O)=O.[Na+]>[Cl:8][C:9]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:10]=1[CH:11]=[CH2:2]

Participants

6

Reactant 3

HCID 5460504PhosphoniumHCID 93617462-Chloro-4-methoxybenzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 90456012HCID 90456012, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a suspension of phosphonium salt (2.05 g, 5 mmol) in THF (50 mL), was added t-BuOK (0.84 g, 7.5 mmol). The mixture turned to yellow and was kept stirring at RT for 1 h. 2-Chloro-4-methoxybenzaldehyde (0.85 g, 5 mmol) was added to the mixture. The mixture was stirred for 24 h, diluted with sat. NaHCO3 and then extracted with hexane. Organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by Isolera One (100% hexanes to afford the desired product (0.45 g, 53% yield). 1H NMR (CDCl3, δ): 7.49 (d, J=6.8 Hz, 1H), 7.03 (dd, J=8.8, 14.0 Hz, 1H), 6.90 (d, J=2.0, 1H), 6.79 (dd, J=2.0, 6.8 Hz, 1H), 5.62 (d, J=14.0 Hz, 1H), 5.26 (d, J=8.8 Hz, 1H), 3.80 (s, 3H).

Workup

  1. stirringThe mixture was stirred for 24 h
  2. extractionextracted with hexane
  3. dry with materialOrganic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by Isolera One (100% hexanes

Sources & evidence

ORD record
ord-f1fb33f26ac640f8b27e9dcf042cac18
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

Loading…