Tetrahydrofuran → HCID 67253869, compound

HRID 1948004Notes

Reaction equation

HRID 1948004 reaction equation
Cl[CH:2](Cl)[CH2:3][PH2:4].[O-:6][CH2:7][CH3:8].[Na+].[N+:10]([C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1)([O-:12])=[O:11].C1C[O:24]CC1>>[CH2:3]([P:4]([CH2:17][C:16]1[CH:19]=[CH:20][C:13]([N+:10]([O-:12])=[O:11])=[CH:14][CH:15]=1)(=[O:24])[O:6][CH2:7][CH3:8])[CH3:2]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 660114-Nitrobenzyl bromideHCID 2723922Sodium ethoxideHCID 53428250HCID 53428250, compound

Product 1

HCID 67253869HCID 67253869, compound

Procedure

A solution of dichloroethylphosphine (2.5 g, 19 mmol) in THF (11 mL) was slowly charged with sodium ethoxide (2.86 g, 42.0 mmol) at 0° C. and stirred for 15 min. The reaction mixture was charged with p-nitrobenzylbromide (4.1 g, 19 mmol) in a sealed tube and stirred at 100° C. over night. The reaction mixture was concentrated in vacuo and the residue was purified on an Isco Combiflash unit eluting with 0 to 5% MeOH in DCM to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.19 (d, J=8.34 Hz, 2H), 7.55 (dd, J=2.02, 8.84 Hz, 2H), 3.83-4.04 (m, 2H), 3.41 (d, J=16.93 Hz, 2H), 1.58-1.73 (m, 2H), 1.16 (t, J=7.07 Hz, 3H), 0.94-1.06 (m, 3H).

Workup

  1. stirringstirred at 100° C. over night
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified on an Isco Combiflash unit
  4. washeluting with 0 to 5% MeOH in DCM

Sources & evidence

ORD record
ord-490a0317dac64e77a41558850b240bd8
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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