Boron trifluoride etherate → HCID 54257178, compound

HRID 1612784Notes

Reaction equation

HRID 1612784 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:15])=[CH:9][PH:10](=[O:14])[O:11][CH2:12][CH3:13])=[CH:4][CH:3]=1.B(F)(F)F.CCOCC.C(=O)([O-])O.[Na+].[CH:30](OCC)([O:34][CH2:35][CH3:36])[O:31][CH2:32][CH3:33]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:15])=[CH:9][P:10]([CH:30]([O:34][CH2:35][CH3:36])[O:31][CH2:32][CH3:33])(=[O:14])[O:11][CH2:12][CH3:13])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 8000Boron trifluoride etherateHCID 31214Ethyl orthoformateHCID 516892Sodium BicarbonateHCID 178476801HCID 178476801, compound

Product 1

HCID 54257178HCID 54257178, compound

Procedure

A solution of 1.68 g of ethyl 2-(4-chlorophenyl)prop-1-enylphosphinate in 20 ml of triethyl orthoformate is treated with 0.1 g of boron trifluoride diethyl etherate and the resulting solution stirred for 7 days at room temperature. The reaction mixture is then treated with 20 ml 10% aqueous sodium hydrogen carbonate solution and extracted twice with dichloromethane. The organic layer is removed, dried and concentrated to give an oil. Chromatography on silica gel gives ethyl 2-(4-chlorophenyl)prop-1-enyl-(diethoxymethyl)phosphinate as a colourless oil. 1H-NMR (CDCl3): δ(ppm)=7.38 (4H, m; Ph), 5.51 (1H, d, CH), 4.62 (1H, d, CH--P), 4.05 (2H, q, CH2OP), 3.88-3.56 (CH, m, 2×CH2OC), 2.07 (2H, d, d, CH2P), 1.28-1.14 (9H, m, 3×CH3).

Workup

  1. extractionextracted twice with dichloromethane
  2. customThe organic layer is removed
  3. customdried
  4. concentrationconcentrated
  5. customto give an oil

Sources & evidence

ORD record
ord-553b22b701154d608d1174671f1b5804
Source dataset
uspto-grants-1993_03
Patent number
US05190934

Reaction notes

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