Hydrochloric Acid → HCID 9903422, compound

HRID 377177Notes

Reaction equation

HRID 377177 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]1C=CC=CC=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>[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])[CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

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

Product 1

HCID 9903422HCID 9903422, compoundYield 154.3%

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, dired 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, 1 H), 1.9-2.0 (m, 2 H), 2.1-2.4 (m, 6 H), 2.7-2.9 (m, 1 H), 3.05 (dd, J=9.0, 16.8 Hz, 2 H), 4.8-5.1 (m, 6 H), 7.0-7.1 (m, 4 H), 7.2-7.4 (m, 15 H).

Workup

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

Sources & evidence

ORD record
ord-9a139e73ecb44ccaa8137f30fae7d2e4
Source dataset
uspto-grants-2000_02
Patent number
US06025344

Reaction notes

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