Imidazole → HCID 90391699, compound

HRID 1056477Notes

Reaction equation

HRID 1056477 reaction equation
[CH:1]1([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]O)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]#[C:2]1.N1C=CN=C1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[I:41]I>C1COCC1.CCCCCC>[I:41][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][O:9][CH:1]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]#[C:2]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 90390643HCID 90390643, compound

Product 1

HCID 90391699HCID 90391699, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a magnetically stirred solution of 6-(cyclooct-2-yn-1-yloxy)hexan-1-ol (126 mg, 0.566 mmol, 1 eq) in dry THF (1.5 ml) under Ar atmosphere, Imidazole (1.1 eq, 0.622 mmol, 42 mg) and Ph3P (1.3 eq, 0.736 mmol, 193 mg) were added. The solution was cooled to 0° C. and Iodine (0.680 mmol, 1.2 eq, 173 mg) was added in three portions. Solution was warmed to RT and stirred for 4 h. The reaction was monitored by TLC (hexane 100% as eluent), quenched by addition of a saturated solution of Na2SO3 (3 ml) and the phases were separated. The aqueous phase was extracted with Et2O and combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum. The obtained raw product was purified using a column of silica gel (40 g) and Hexane as eluent to obtain 3-[(6-iodohexyl)oxy]cyclooct-1-yne.

Workup

  1. temperatureSolution was warmed to RT
  2. customquenched by addition of a saturated solution of Na2SO3 (3 ml)
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with Et2O
  5. dry with materialwere dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe obtained raw product
  9. customwas purified

Sources & evidence

ORD record
ord-9db23d3b359a448fb330ac4a4ac095ae
Source dataset
uspto-grants-2016_07
Patent number
US09399077B2

Reaction notes

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