Sodium Iodide → Methyl 2-acetyl-7-(3-bromopropoxy)-8-n-propylchroman-2-carboxylate

HRID 1285265Notes

Reaction equation

HRID 1285265 reaction equation
[C:1]([C:4]1([C:18]([O:20][CH3:21])=[O:19])[CH2:13][CH2:12][C:11]2[C:6](=[C:7]([CH2:15][CH2:16][CH3:17])[C:8]([OH:14])=[CH:9][CH:10]=2)[O:5]1)(=[O:3])[CH3:2].[Br:22][CH2:23][CH2:24][CH2:25]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(C(C)=O)C>[C:1]([C:4]1([C:18]([O:20][CH3:21])=[O:19])[CH2:13][CH2:12][C:11]2[C:6](=[C:7]([CH2:15][CH2:16][CH3:17])[C:8]([O:14][CH2:25][CH2:24][CH2:23][Br:22])=[CH:9][CH:10]=2)[O:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 20250456Methyl 2-acetyl-7-hydroxy-8-n-propylchroman-2-carboxylate

Product 1

HCID 20250465Methyl 2-acetyl-7-(3-bromopropoxy)-8-n-propylchroman-2-carboxylateYield 44%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A 50 ml single neck round bottom flask was charged with 640 mg (2.2 mmole) of the compound from Example 39, 6.63 g or 3.33 ml (32.8 mmole) of 1,3-dibromopropane, 690 mg (5 mmole) of anhydrous potassium carbonate, 150 mg (1 mmole) of sodium iodide, and 4 ml of methyl ethyl ketone. The flask was equipped with a magnetic stirring bar and a condenser topped with a calcium chloride drying tube, and refluxed with stirring for 72 hours. The insoluble solids were removed by filtration and the filtrate was concentrated by rotary evaporation. Purification of the residual oil by high pressure liquid chromatography (15% ethyl acetate-hexane) gave 400 mg (44%) of the title compound as a clear oil, homogenous by this layer chromatrography (20% ethyl acetate-hexane).

Workup

  1. customThe flask was equipped with a magnetic stirring bar and a condenser
  2. customtopped with a calcium chloride drying tube
  3. temperaturerefluxed
  4. customThe insoluble solids were removed by filtration
  5. concentrationthe filtrate was concentrated by rotary evaporation
  6. customPurification of the residual oil by high pressure liquid chromatography (15% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-4588a52df47e4343aba0993389e29f7b
Source dataset
uspto-grants-1986_01
Patent number
US04565882

Reaction notes

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