Sodium hydride → HCID 86678258, compound

HRID 1504746Notes

Reaction equation

HRID 1504746 reaction equation
[S].[H-].[Na+].C([N-][CH:8]([CH3:10])[CH3:9])(C)C.[Li+].C=[C:13]([P:20](=[O:59])([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>[P].C1COCC1>[CH2:13]([P:20](=[O:59])([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[CH2:14][CH:15]([P:20](=[O:59])([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:10][CH2:8][CH3:9])[O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 24758Sodium hydride2×HCID 2724682Lithium diisopropylamideHCID 5362487SulfurHCID 86678259HCID 86678259, compound

Product 1

HCID 86678258HCID 86678258, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 5462309PhosphorusSolvent

Procedure

Dioctadecyl hydrogen phosphonate may be reacted with dioctadecyl oct-1-en-2-ylphosphonate to produce tetra-octadecyl heptane-1,3-diyldiphosphonate, J, using substantially the conditions found in Phosphorus, Sulfur and Silicon and the Related Elements, 83 (1-4), 77-98:1993. (See FIG. 9) Thus, dioctadecyl hydrogen phosphonate (MW 586.95, 1.56 g, 2.66 mmol), dissolved in THF (6 mL) and sodium hydride (95%, FW 24.0, 2.66 mmol, 0.064 g) are allowed to react under inert atmosphere at RT with stirring. Alternatively, sodium hydride may be replaced by molar equivalence of strong bases such as lithium di-isoproylamide or sodium alkoxide or the like. Then dioctadecyl oct-1-en-2-ylphosphonate, A, (MW 697.15, 1.88 g, 2.69 mmol) is added and allowed to react under an inert atmosphere until the reaction is complete. The reaction progress may be followed by TLC, hplc or 31P nmr. At the completion of reaction the solvent may be removed by evaporation and the crude product purified by normal phase flash chromatography using a suitable solvent system (e.g., hexanes-ethyl acetate gradient (ELSD detection) to yield substantially pure tetraoctadecyl heptane-1,3-diyldiphosphonate. The crude product may also be purified using rphplc (C4, 300 A, and suitable a solvent gradient. The mass of the desired product is 1270.1.

Workup

  1. customto react under inert atmosphere at RT
  2. customto react under an inert atmosphere until the reaction
  3. customAt the completion of reaction the solvent
  4. custommay be removed by evaporation
  5. customthe crude product purified by normal phase flash chromatography

Sources & evidence

ORD record
ord-23383de2866d408d9b6b0bd33408d444
Source dataset
uspto-grants-2015_12
Patent number
US09216225B2

Reaction notes

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