Imidazole → HCID 69374586, compound

HRID 917315Notes

Reaction equation

HRID 917315 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.[C:27]([O:31][C:32](=[O:42])[CH2:33][O:34][CH:35]1[CH2:40][CH2:39][CH:38](O)[CH2:37][CH2:36]1)([CH3:30])([CH3:29])[CH3:28]>C(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[C:27]([O:31][C:32](=[O:42])[CH2:33][O:34][CH:35]1[CH2:40][CH2:39][CH:38]([I:25])[CH2:37][CH2:36]1)([CH3:30])([CH3:29])[CH3:28]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 54282468HCID 54282468, compound

Product 1

HCID 69374586HCID 69374586, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (1.18 g, 4.49 mmol), imidazole (0.31 g, 4.49 mmol) and iodine (1.14 g, 4.49 mmol) are added to a solution of (4-hydroxy-cyclohexyloxy)-acetic acid tert-butyl ester (cis:trans=ca. 1:1) (0.86 g, 3.74 mmol) in a mixture of CH2Cl2 (10 ml)/CCl4 (20 ml) at 0° C. The cooling bath is removed and the reaction mixture is stirred at room temperature for 18 hours. Saturated aq. Na2S2O3 (10 ml) is added and the mixture is stirred for 15 minutes. The layers are separated and the aqueous layer is re-extracted with CH2Cl2 (×3). The combined organic extracts are washed with brine (×1), dried (Na2SO4), filtered and concentrated. Purification by chromatography on silica gel, eluting with 5% ethyl acetate in isohexane, gives the product.

Workup

  1. customThe cooling bath is removed
  2. additionSaturated aq. Na2S2O3 (10 ml) is added
  3. stirringthe mixture is stirred for 15 minutes
  4. customThe layers are separated
  5. extractionthe aqueous layer is re-extracted with CH2Cl2 (×3)
  6. washThe combined organic extracts are washed with brine (×1)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by chromatography on silica gel
  11. washeluting with 5% ethyl acetate in isohexane
  12. customgives the product

Sources & evidence

ORD record
ord-134739a07c7d4173b4e32ea84b00bc66
Source dataset
uspto-grants-2007_09
Patent number
US07273875B2

Reaction notes

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