Sodium hydride → HCID 9949326, compound

HRID 1934337Notes

Reaction equation

HRID 1934337 reaction equation
CC1C=CC(CP(=O)OCC2C=CC=CC=2)=CC=1.[H-].[Na+].C([O:28][C:29]([CH:31]([CH2:45][CH2:46][C:47]([O:49]CC1C=CC=CC=1)=[O:48])[CH2:32][P:33]([CH2:36][CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)(=[O:35])[OH:34])=[O:30])C1C=CC=CC=1>C1COCC1.CCOC(C)=O>[C:39]1([CH2:38][CH2:37][CH2:36][P:33]([CH2:32][CH:31]([CH2:45][CH2:46][C:47]([OH:49])=[O:48])[C:29]([OH:30])=[O:28])([OH:35])=[O:34])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 18403163HCID 18403163, compoundHCID 178425928HCID 178425928, compound

Product 1

HCID 9949326HCID 9949326, compoundYield 163%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-methylbenzyl-O-benzylphosphinic acid (2, R=4-methylbenzyl) (2.16 g, 8.3 mmol) in THF (15 Ml) was added sodium hydride (0.10 g, 60% dispersion in oil) followed by dibenzyl 2-methylenepentanedioate (3) (3.24 g) at 0° C., and the mixture was stirred at room temperature for 4 hours. The reaction mixture was then diluted with EtOAc (50 Ml) and poured into 1 N Hcl (50 Ml). The organic layer was separated, dried over Na2SO4, and concentrated. This material was purified by silica gel chromatography (hexanes: EtOAc, 4:1 to 1:1) to give 3.41 g of 2,4-di(benzyloxycarbonyl)-butyl(4-methylbenzyl)-o-benzylphosphinic acid (4, R=4-methylbenzyl) as colorless oil (70% yield). Rf 0.61 (EtOAc).

Workup

  1. additionpoured into 1 N Hcl (50 Ml)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThis material was purified by silica gel chromatography (hexanes: EtOAc, 4:1 to 1:1)

Sources & evidence

ORD record
ord-2bf9ab68af884e728ce8819547ec9d0e
Source dataset
uspto-grants-2002_05
Patent number
US06384022B1

Reaction notes

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