Sodium Iodide → HCID 20250460, compound

HRID 1285262Notes

Reaction equation

HRID 1285262 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[C:6]([CH2:14][CH2:15][CH3:16])[C:7]([OH:13])=[CH:8][CH:9]=2)[O:4]1.[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(C(C)=O)C>[OH:1][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[C:6]([CH2:14][CH2:15][CH3:16])[C:7]([O:13][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][Br:17])=[CH:8][CH:9]=2)[O:4]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 20250467HCID 20250467, compound

Product 1

HCID 20250460HCID 20250460, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A 250 ml single neck round bottom flask was charged with 2.70 g (12.15 mmole) of the compound from Example 34, 42 g or 25 ml (182 mmole) of 1,5-dibromopentane, 2.07 g (15 mmole) of anhydrous potassium carbonate, 750 mg (5 mmole) of sodium iodide, and 150 ml of methyl ethyl ketone. The flask was fitted with a magnetic stirring bar and a condenser topped with a calcium chloride drying tube and the reaction was refluxed for 5 days. The undissolved solids were removed by filtration and the filtrate was concentrated in vacuo on a rotary evaporator. The crude liquid residue was purified by high pressure liquid chromatography (20% ethyl acetate-hexane) to give 2.69 g (82%) of the title compound as a light yellow oil. Calc: C, 58.22; H, 7.33; Found: C, 58.10; H, 7.24.

Workup

  1. customThe flask was fitted with a magnetic stirring bar and a condenser
  2. customtopped with a calcium chloride drying tube
  3. temperaturethe reaction was refluxed for 5 days
  4. customThe undissolved solids were removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo on a rotary evaporator
  6. customThe crude liquid residue was purified by high pressure liquid chromatography (20% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-c5e2fc8887374eb5b9d9e8edcb0a25f7
Source dataset
uspto-grants-1986_01
Patent number
US04565882

Reaction notes

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