Hydrochloric Acid → HCID 9949326, compound

HRID 849027Notes

Reaction equation

HRID 849027 reaction equation
C([O:8][C:9]([CH:11]([CH2:25][CH2:26][C:27]([O:29]CC1C=CC=CC=1)=[O:28])[CH2:12][P:13]([CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:15])[OH:14])=[O:10])C1C=CC=CC=1.[H-].[Na+].C=C(CCC(OCC1C=CC=CC=1)=O)C(OCC1C=CC=CC=1)=O.Cl>C1COCC1.CCOC(C)=O>[C:19]1([CH2:18][CH2:17][CH2:16][P:13]([CH2:12][CH:11]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])[C:9]([OH:10])=[O:8])([OH:15])=[O:14])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 10947302Dibenzyl 2-methylenepentanedioateHCID 18403163HCID 18403163, compound

Product 1

HCID 9949326HCID 9949326, compoundYield 125.1%

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 at 0 C., and the mixture was stirred at rt for 4 h. 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): Rf 0.61 (EtOAc); 1H NMR (CDCl3) delta 1.6-1.8 (m, 1H), 1.9-2.0 (m, 2H), 2.1-2.4 (m, 6H), 2.7-2.9 (m, 1H), 3.05 (dd, J=9.0, 16.8 Hz, 2H), 4.8-5.1 (m, 6H), 7.0-7.1 (m, 4H), 7.2-7.4 (m, 15H).

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-e97e5902c3424df28f82c477cb13c07f
Source dataset
uspto-grants-2000_01
Patent number
US06011021

Reaction notes

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