Water → Di-tert-butyl 2-[[[2-(benzylcarboxy)propyl]tert-butoxyphosphinyl]methyl]pentanedioate

HRID 1976711Notes

Reaction equation

HRID 1976711 reaction equation
[C:1]([O:5][PH:6]([CH2:8][CH:9]([CH2:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:26]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:30])[C:27]([CH3:29])=[CH2:28].[H-].[Na+].O>C1COCC1.CCOCC>[CH2:32]([O:31][C:26]([CH:27]([CH3:29])[CH2:28][P:6]([CH2:8][CH:9]([CH2:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:30])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 962WaterHCID 17236Benzyl methacrylateHCID 24758Sodium hydrideHCID 178451016HCID 178451016, compound

Product 1

HCID 18418074Di-tert-butyl 2-[[[2-(benzylcarboxy)propyl]tert-butoxyphosphinyl]methyl]pentanedioateYield 53%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of di-tert-butyl 2-[(tert-butoxy-phosphinyl)methyl]pentane-1,5-dioate (13.62 g, 36.0 mmol) and benzyl methacrylate (6.35 g, 36.0 mmol) in THF (100 ml) under nitrogen was added sodium hydride (0.14 g, 60% dispersion in oil, 3.60 mmol). After three hours, the reaction mixture was poured into water (300 ml) and ether (100 ml) was added. The organic layer was separated and retained, and the aqueous layer was washed again with ether (100 ml). The combined organic extracts were dried over magnesium sulfate and the solvent was removed under reduced pressure. The resulting residue was purified by column chromatography and the product was eluted with 2:3 EtOAc/Hexane. The solvent was removed under reduced pressure leaving a clear oil (10.5 g, 53%). 1H NMR (CDCl3): δ 1.3 (m, 3H), 1.5 (m, 27H), 1.7 (m, 2H), 1.9 (m, 2H), 2.2 (m, 4H), 2.6 (m, 1H), 2.9 (m, 1H), 5.1 (m, 2H), 7.3 (m, SH).

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washthe aqueous layer was washed again with ether (100 ml)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe resulting residue was purified by column chromatography
  7. washthe product was eluted with 2:3 EtOAc/Hexane
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-41616e3ebbf74341b82b38fe45e61d5e
Source dataset
uspto-grants-2001_05
Patent number
US06228888B1

Reaction notes

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