Hydrochloric Acid → HCID 9949326, compound

HRID 850306Notes

Reaction equation

HRID 850306 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.Cl>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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 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 1N 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). R.function.0.61 (EtOAc).

Workup

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

Sources & evidence

ORD record
ord-3ed6e87979704daaa61b893011f1b19f
Source dataset
uspto-grants-2000_01
Patent number
US06017903

Reaction notes

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