Imidazole → Methyl 7-iodohept-5-ynoate

HRID 2264643Notes

Reaction equation

HRID 2264643 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 min., the dichloromethane was evaporated in vacuo to a few mL's 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 a few mL's
  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-b4bef2a3a9554dc599bac5f41a74bf91
Source dataset
uspto-grants-2010_12
Patent number
US07855226B2

Reaction notes

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