Imidazole → HCID 68710266, compound

HRID 1911559Notes

Reaction equation

HRID 1911559 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2([CH2:37]O)[CH2:36][CH2:35]2)=[CH:30][CH:29]=1>ClCCl>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2([CH2:37][I:25])[CH2:36][CH2:35]2)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 27240201-(p-Chlorophenyl)cyclopropanemethanol

Product 1

HCID 68710266HCID 68710266, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of triphenylphosphine (3.45 g, 13 mmol) and imidazole (0.90 g, 13 mmol) in dichloromethane (25 ml) under an argon atmosphere was added slowly iodine (3.33 g, 13 mmol) and [1-(4-chlorophenyl)-cyclopropyl]-methanol (2.00 g, 11 mmol). The mixture was stirred for 2 hours at room temperature, then dichloromethane (75 ml) was added and mixture was extracted with saturated sodium thiosulfate solution (100 ml) and hydrochloric acid (1N, 50 ml). The organic layer was dried over MgSO4 and evaporated. The residue was suspended in ether and filtered to remove insoluble triphenylphosphine oxide. The ether was evaporated and the residue was purified by column chromatography (SiO2, heptane/EtOAc=9:1) to yield a light yellow oil, (2.30 g, 72%); MS (EI): 292.0 (M+.).

Workup

  1. extractionmixture was extracted with saturated sodium thiosulfate solution (100 ml) and hydrochloric acid (1N, 50 ml)
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated
  4. filtrationfiltered
  5. customto remove insoluble triphenylphosphine oxide
  6. customThe ether was evaporated
  7. customthe residue was purified by column chromatography (SiO2, heptane/EtOAc=9:1)
  8. customto yield a light yellow oil, (2.30 g, 72%)

Sources & evidence

ORD record
ord-c694ef49607b4e8aafa95af2c86a501f
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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