Ammonium Chloride → HCID 178527033, compound

HRID 847583Notes

Reaction equation

HRID 847583 reaction equation
[C:1]1([CH2:7][CH2:8][Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[P:11]([O-:18])(OCC)OCC.[Cl-].[NH4+]>C(OCC)C>[C:1]1([CH2:7][CH2:8][PH:11](=[O:18])[CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 3780918DiethylphosphiteHCID 178419670HCID 178419670, compound

Product 1

HCID 178527033HCID 178527033, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 25 mmol of (2-phenyl)ethylmagnesium bromide in 25 ml of diethyl ether was added dropwise with cooling (ice bath) 0.92 ml (7.14 mmol) of diethyl phosphite. The resulting solution was heated at reflux for 2 h, cooled, and treated with aqueous ammonium chloride. The product was extracted with ether, dried over MgSO4, and concentrated in vacuo. Flash chromatography using ethyl acetate gave 1.23 g (64%) of the desired compound (Rf 0.64, 10% methanol in chloroform) as a colorless oil. 1H NMR (CDCl3) δ 2.0-2.2 (m, 4H), 2.85-3.1 (m, 4H), 6.89 (dm, J=455 Hz, 1H), 7.15-7.4 (m, 10H). Mass spectrum (M+H)+ =259.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 2 h
  3. temperaturecooled
  4. extractionThe product was extracted with ether
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d98e138e3b234b2694c6bb85f48f9819
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

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