Imidazole → HCID 25138734, compound

HRID 1950741Notes

Reaction equation

HRID 1950741 reaction equation
[CH3:1][CH2:2][O:3][P:4]([O:19][CH2:20][CH3:21])([CH:6]([P:11]([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:8][CH2:9]O)=[O:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:46]I>C(Cl)Cl>[CH3:1][CH2:2][O:3][P:4]([O:19][CH2:20][CH3:21])([CH:6]([P:11]([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:8][CH2:9][I:46])=[O:5]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 153967034,4-Bis(Diethoxyphosphoryl)butan-1-ol

Product 1

HCID 25138734HCID 25138734, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 32 (1.52 g, 4.39 mmol) in CH2Cl2 (50 mL) were added triphenylphosphine (1.32 g, 5.033 mmol) and imidazole (0.45 g, 6.61 mmol). The reaction mixture was cooled to 0° C., before the addition of iodine (1.22 g, 4.81 mmol). The mixture was then removed from the cooling bath, stirred for 2 h, diluted with hexanes (100 mL) and filtered washing the precipitate with further hexanes (2×30 mL). The filtrate was evaporated and purified by flash chromatography on silica gel with gradient elution from 0-10% methanol/ethyl acetate to give pure 33 (1.6 g, 80%). 1H NMR (400 MHz, CDCl3) δ 1.32-1.38 (m, 12H), 1.95-2.15 (m, 4H), 2.28 (tt, J=24.1, 6.1, 1H), 3.18 (t, J=6.6, 2H), 4.12-4.24 (m, 8H).

Workup

  1. customThe mixture was then removed from the cooling bath
  2. additiondiluted with hexanes (100 mL)
  3. filtrationfiltered
  4. washwashing the precipitate with further hexanes (2×30 mL)
  5. customThe filtrate was evaporated
  6. custompurified by flash chromatography on silica gel with gradient elution from 0-10% methanol/ethyl acetate

Sources & evidence

ORD record
ord-3a86d47937e04ad18ebfab370a77c5d9
Source dataset
uspto-grants-2013_03
Patent number
US08404664B2

Reaction notes

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