Imidazole → Methyl 7-iodohept-5-ynoate

HRID 2364895Notes

Reaction equation

HRID 2364895 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][C:7]#[C:8][CH2:9]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:36]I>ClCCl>[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][C:7]#[C:8][CH2:9][I:36]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 11789443Methyl 7-hydroxyhept-5-ynoate

Product 1

HCID 10901527Methyl 7-iodohept-5-ynoateYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (30) (1.347 g, 8.6 mmol) in 5 mL dichloromethane was added to a mixture of triphenylphosphine (2.725 g, 10.4 mmol), imidazole (726 mg, 10.7 mmol), and iodine (2.602 g, 10.3 mmol) in 34 mL dichloromethane, rinsing with 5 mL dichloromethane. After 40 minutes, the dichloromethane was evaporated in vacuo to about 2 mL and the resulting mixture filtered through basic alumina, washing with 10% ethyl acetate/hexanes. Purification by flash chromatography on silica gel (10% ethyl acetate/hexanes) gave 1.878 g (7.1 mmol, 83%) of the propargyl iodide.

Workup

  1. washrinsing with 5 mL dichloromethane
  2. customthe dichloromethane was evaporated in vacuo to about 2 mL
  3. filtrationthe resulting mixture filtered through basic alumina
  4. washwashing with 10% ethyl acetate/hexanes
  5. customPurification by flash chromatography on silica gel (10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-01cb46a1c1074a47bbda0058805a5441
Source dataset
uspto-grants-2014_04
Patent number
US08697057B2

Reaction notes

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