Sodium Carbonate → Ethyl 3-oxo-4-(triphenyl-lambda~5~-phosphanylidene)butanoate

HRID 1267804Notes

Reaction equation

HRID 1267804 reaction equation
[Cl-].[CH2:2]([O:4][C:5]([CH2:7][C:8](=[O:29])[CH2:9][P+:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:6])[CH3:3].C(=O)([O-])[O-].[Na+].[Na+]>O>[CH2:2]([O:4][C:5]([CH2:7][C:8](=[O:29])[CH:9]=[P:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:6])[CH3:3]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 2773640[3-(Ethoxycarbonyl)-2-oxopropyl]triphenylphosphonium chloride

Product 1

HCID 2734128Ethyl 3-oxo-4-(triphenyl-lambda~5~-phosphanylidene)butanoateYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of {3-(ethoxycarbonyl)-2-oxopropyl}triphenyl phosphonium chloride (21.34 g, 500 mmol) in water (450 mL) was added to a solution of sodium carbonate (3.1 g, 25.0 mmol) in 10 min (Note: A white precipitate was obtained immediately after the addition). This reaction mixture was stirred at room temperature overnight. The precipitate that obtained was filtered off through a sintered funnel. The precipitate was dissolved in dichloromethane (100 mL), dried over sodium sulfate and concentrated to yield a white solid 18.13 g (93%). This material was dried over phosphorus pentoxide overnight. 1H NMR (CDCl3) δ 1.26 (t, 3H), 3.34 (s, 2H), 3.76-3.84 (d, 1H) 4.19 (m, 2H) and 7.48-7.68 (m, 15H, PhH).

Workup

  1. customA white precipitate was obtained immediately
  2. additionafter the addition)
  3. customThe precipitate that obtained
  4. filtrationwas filtered off through a sintered funnel
  5. dissolutionThe precipitate was dissolved in dichloromethane (100 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4b6e899a8df643079fa07a163816c47d
Source dataset
uspto-grants-2003_04
Patent number
US06552183B1

Reaction notes

Loading…