Water → HCID 86684927, compound

HRID 1844756Notes

Reaction equation

HRID 1844756 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].O.ClP(Cl)[CH2:21][CH2:22][P:23](Cl)Cl.[CH2:27]1[CH2:31]O[CH2:29][CH2:28]1>>[CH2:1]([P:23]([CH:22]([P:23]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:22][CH2:21][CH2:31][CH2:27][CH2:28][CH2:29][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH3:21])[CH2:29][CH2:28][CH2:27][CH2:31][CH2:31][CH2:27][CH2:28][CH2:29][CH2:31][CH2:27][CH2:28][CH2:29][CH2:12][CH2:11][CH3:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 4

HCID 962Water2×HCID 8028TetrahydrofuranHCID 119904Phosphonous dichloride, 1,2-ethanediylbis-HCID 178443133HCID 178443133, compound

Product 1

HCID 86684927HCID 86684927, compound

Conditions

Temperature
-30 °C

Procedure

250 ml of pentadecylmagnesium bromide (15% in tetrahydroluran (THF); 119 mmol) are initially charged in a 1|4-neck flask with internal thermometer, argon blanketing, metal/water condenser and stirrer, and cooled to −30° C. Subsequently, a solution of 5.5 g (23.8 mmol) of 1,2-bis(dichlorophosphino)-ethane in 100 ml of THF is added dropwise within 30 minutes, in the course of which a large amount of solids precipitates. The mixture is then warmed to room temperature within one hour and subsequently stirred at internal temperature 50° C. for a further 2 hours, which gives rise to a grayish-white suspension. This is admixed gradually, and while cooling with ice, with 95 ml of saturated and degassed NH4Cl solution to obtain a white suspension. Another 65 ml of degassed water are added thereto and the precipitate is filtered off with suction through a G2 frit under argon. The product is washed once with water and twice with 20 ml of THF, and dried under reduced pressure. This gives 22.2 g (93.5%) of the product in the form of a white powder. 31P NMR (CDCl3): −26.8 ppm (s); elemental analysis: calc. C 79.6%, H 13.8%, P 6.6%; exp. C 79.5%, H 14.0%, P 6.3%, Br 0.04%, Cl 0.06%, O<0.5%.

Workup

  1. customprecipitates
  2. temperatureThe mixture is then warmed to room temperature within one hour
  3. customwhich gives rise to a grayish-white suspension
  4. temperaturewhile cooling with ice, with 95 ml of saturated and
  5. customdegassed NH4Cl solution
  6. customto obtain a white suspension
  7. filtrationthe precipitate is filtered off with suction through a G2 frit under argon
  8. washThe product is washed once with water and twice with 20 ml of THF
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-cdec9ace95ba4ad096880116a5c5dfa5
Source dataset
uspto-grants-2015_02
Patent number
US08946462B2

Reaction notes

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