Iodine chloride → 2-(1-iodoethyl)-2-(6-methoxy-2-naphthyl)-1,3-dioxolane-4(R),5(R)-dicarboxylic acid dimethyl ester

HRID 2309853Notes

Reaction equation

HRID 2309853 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[C@H:9]([C:10]([O:12][CH3:13])=[O:11])[O:8][C:7]([CH2:26][CH3:27])([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH3:25])[CH:20]=3)[CH:15]=2)[O:6]1)=[O:4].[I:28]Cl.C(=O)(O)[O-].[Na+].COC([C@H]1[C@H](C(OC)=O)OCO1)=O>ClCCl>[CH3:13][O:12][C:10]([C@H:9]1[C@H:5]([C:3]([O:2][CH3:1])=[O:4])[O:6][C:7]([CH:26]([I:28])[CH3:27])([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH3:25])[CH:20]=3)[CH:15]=2)[O:8]1)=[O:11]

Participants

6

Reactant 4

HCID 24640Iodine chlorideHCID 516892Sodium BicarbonateHCID 108616772-ethyl-2-(6-methoxy-2-naphthyl)-1,3-dioxolane-4(R),5(R)-dicarboxylic acid dimethyl esterHCID 151906411,3-dioxolane-4(R),5(R)-dicarboxylic acid dimethyl ester

Product 1

HCID 156142782-(1-iodoethyl)-2-(6-methoxy-2-naphthyl)-1,3-dioxolane-4(R),5(R)-dicarboxylic acid dimethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2 -ethyl-2-(6-methoxy-2-naphthyl)-1,3-dioxolane-4(R),5(R)-dicarboxylic acid dimethyl ester (0.935 g, 2.5 mmol) and of iodine monochloride (0.81 g, 5 mmol) in dichloromethane (5 ml) is kept under nitrogen and at 15° C. for 24 hours. The reaction mixture is poured into a 10% aqueous solution of sodium bicarbonate, and extracted with additional dichloromethane. The combined organic extracts are washed with a 5% aqueous solution of sodium thiosulphate, with water, dried (Na2SO4), filtered, and concentrated in vacuo. Purification of the residue by column chromatography (silical gel, eluent hexane:diethyl ether=7:3) gives the diastereoisomeric mixture of 2-(1-iodoethyl)-1-iodoethyl)-2-methoxy-2-naphthyl)-1,3-dioxolane-4(R),5(R)-dicarboxylic acid dimethyl ester 15 and 16 in ratio 15:16=60:40 (determined by 1H-NMR).

Workup

  1. extractionextracted with additional dichloromethane
  2. washThe combined organic extracts are washed with a 5% aqueous solution of sodium thiosulphate, with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by column chromatography (silical gel, eluent hexane:diethyl ether=7:3)
  7. customgives

Sources & evidence

ORD record
ord-37e224f76fec4ac48d8fb9c450d6d3a5
Source dataset
uspto-grants-1987_09
Patent number
US04697036

Reaction notes

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