Chloroiodomethane → Benzyl chloromethyl pentanedioate

HRID 1461996Notes

Reaction equation

HRID 1461996 reaction equation
[CH2:1]([O:8][C:9](=[O:16])[CH2:10][CH2:11][CH2:12][C:13]([O-:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:34][CH2:35]I>>[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:16])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:35][Cl:34])=[O:14]

Participants

3

Reactant 2

HCID 11644ChloroiodomethaneHCID 14479933HCID 14479933, compound

Product 1

HCID 19692005Benzyl chloromethyl pentanedioateYield 62.5%

Procedure

A mixture of 1.5 g (3.75 mmole) tetrabutylammonium benzyl glutarate and 20 ml chloroiodomethane is stirred at room temperature for three hours and concentrated in vacuo to a viscous oil. The oil is taken up in 20 ml ethyl acetate and 30 ml hexane and filtered to remove tetrabutylammonium iodide. The solvent is evaporated in vacuo and the residue purified by chromatography on 75 g silica gel, eluting with 70:30 ethyl acetate/hexane by volume. Fractions (15 ml) were collected every 0.7 minutes. The fractions containing the desired product (fractions 8-11) are combined and the solvent evaporated in vacuo to yield 0.55 g (62.5%) of the desired product. 1H-NMR (CDCl3) ppm (delta): 1.65-2.2 (m, 2H), 2.26-2.64 (m, 4H), 5.1 (s, 2H), 5.65 (s, 2H), 7.3 (s, 5H).

Workup

  1. concentrationconcentrated in vacuo to a viscous oil
  2. filtration30 ml hexane and filtered
  3. customto remove tetrabutylammonium iodide
  4. customThe solvent is evaporated in vacuo
  5. customthe residue purified by chromatography on 75 g silica gel
  6. washeluting with 70:30 ethyl acetate/hexane by volume
  7. customFractions (15 ml) were collected every 0.7 minutes
  8. additionThe fractions containing the desired product (fractions 8-11)
  9. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-705904701c3e4883a5ae32e2d047941d
Source dataset
uspto-grants-1984_07
Patent number
US04457924

Reaction notes

Loading…