Sodium hydride → 4-(Bis-benzyloxy-phosphoryl)-butyric acid ethyl ester

HRID 902934Notes

Reaction equation

HRID 902934 reaction equation
[H-].[Na+].[P:3]([O-:20])([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:21]([O:23][C:24](=[O:29])[CH2:25][CH2:26][CH2:27]Br)[CH3:22]>CN(C=O)C>[CH2:21]([O:23][C:24](=[O:29])[CH2:25][CH2:26][CH2:27][P:3]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:20])[CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 21904359Dibenzylphosphite

Product 1

HCID 109269054-(Bis-benzyloxy-phosphoryl)-butyric acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of NaH (60%, 2.52 g, 63 mmol) in DMF (60 mL) was added dibenzyl phosphite (12 mL, 48.45 mmol). After 15 minutes of stirring, ethyl-4-bromobutyrate was added and the mixture was stirred for 48 h at room temperature. The DMF was removed by evaporation. The residue was partitioned between brine, ammonium chloride and ether. The water phase was extracted several times with ether. The recombined organic layer was extracted with brine, dried over sodium sulfate, filtered and evaporated. The residue was flashed using 50% ethyl acetate in hexanes to afford the product as a colorless oil. 1H-NMR(CDCl3, 400 MHz: 1.23(t, J=7.2 Hz, 3H); 1.77-2.04(m, 4H); 2.37(m, 2H); 4.10(q, J=7.2 Hz, 2H), 5.03(m, 4H); 7.31(m, 10H). 31P-NMR(CDCl3, 400 MHz): 32.78.

Workup

  1. stirringthe mixture was stirred for 48 h at room temperature
  2. customThe DMF was removed by evaporation
  3. customThe residue was partitioned between brine, ammonium chloride and ether
  4. extractionThe water phase was extracted several times with ether
  5. extractionThe recombined organic layer was extracted with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-b78def7f40414490bd368652e2522c43
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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