Diisopropylamine → HCID 86638412, compound

HRID 1662870Notes

Reaction equation

HRID 1662870 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].C(N[CH:10]([CH3:12])[CH3:11])(C)C.[CH2:13]([O:15][P:16]([C:21]1[C:25]([P:26]([O:31][CH2:32][CH3:33])([O:28][CH2:29][CH3:30])=[O:27])=[CH:24][S:23][CH:22]=1)([O:18][CH2:19][CH3:20])=[O:17])[CH3:14].[CH2:34]([Sn:38](Cl)([CH2:43][CH2:44][CH2:45][CH3:46])[CH2:39][CH2:40][CH2:41][CH3:42])[CH2:35][CH2:36][CH3:37].P([O-])([O-])(O)=O.[Na+].[Na+].P([O-])(O)(O)=O.[Na+]>C1COCC1>[CH2:1]([Sn:38]([CH2:39][CH2:12][CH2:10][CH3:11])([CH2:34][CH2:35][CH2:36][CH3:37])[C:24]1[S:23][C:22]([Sn:38]([CH2:43][CH2:44][CH2:45][CH3:46])([CH2:39][CH2:40][CH2:41][CH3:42])[CH2:34][CH2:35][CH2:36][CH3:37])=[C:21]([P:16]([O:18][CH2:19][CH3:20])([O:15][CH2:13][CH3:14])=[O:17])[C:25]=1[P:26]([O:28][CH2:29][CH3:30])([O:31][CH2:32][CH3:33])=[O:27])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 15096Tributyltin ChlorideHCID 59155862HCID 59155862, compoundHCID 86630341Sodium phosphate (Na3(PO4)2)HCID 178418339Butyllithium

Product 1

HCID 86638412HCID 86638412, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Commercially available n-butyl lithium (2.6 M hexane solution, 21.0 mmols) was slowly dropped in a THF solution cooled to −78° C., of 2.14 g (21.0 mmols) of commercially available diisopropylamine. After stirring for 1 hour, a THF solution of 3.00 g (8.41 mmols) of 3,4-bis(diethoxyphosphoryl)thiophene obtained in Example 1 was added. After stirring for further 1 hour at a standing temperature, 8.20 g (25.2 mmols) of commercially available tributylstannyl chloride was dropped, followed by stirring for 4 hours. After completion of the reaction, a disodium hydrogen phosphate/sodium dihydrogen phosphate buffer solution, adjusted to pH=7, was added so as to complete the reaction, followed by extraction with ethyl acetate. The organic phase was washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was removed, and the resulting crude product was purified with a silica gel column (ethyl acetate) to obtain the specified substance in the form of a transparent oil at a yield of 5.58 g (yield: 100%).

Workup

  1. additionwas dropped
  2. stirringby stirring for 4 hours
  3. customAfter completion of the reaction
  4. additionwas added so as
  5. customthe reaction
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic phase was washed with a saturated saline solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was removed
  10. customthe resulting crude product was purified with a silica gel column (ethyl acetate)
  11. customto obtain the specified substance in the form of a transparent oil at a yield of 5.58 g (yield: 100%)

Sources & evidence

ORD record
ord-5888b6ee9cba4e3ca24718817f4e3081
Source dataset
uspto-grants-2011_10
Patent number
US08030438B2

Reaction notes

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