Chloromethyl Methyl Ether → 5-chloromethyl-3H-benzofuran-2-one

HRID 481409Notes

Reaction equation

HRID 481409 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][C:2]1=[O:10].CO[CH2:13][Cl:14].Cl[Sn](Cl)(Cl)Cl>C(Cl)Cl>[Cl:14][CH2:13][C:8]1[CH:7]=[CH:6][C:5]2[O:1][C:2](=[O:10])[CH2:3][C:4]=2[CH:9]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24287Tin tetrachlorideHCID 683822(3H)-Benzofuranone

Product 1

HCID 190662885-chloromethyl-3H-benzofuran-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3H-benzofuran-2-one (7.45 mmol) and chlormethyl methyl ether (9.31 mmol) in 15 ml of CH2Cl2 at 0° C. was slowly added SnCl4 (15 mmol). The reaction was slowly allowed to warm to ambient temperature and was stirred for 2 hours. The reaction was cooled to 0° C. and carefully quenched with saturated sodium bicarbonate. The mixture was extracted (2×EtOAc) and the organics were washed with brine. The combined organics were then dried over MgSO4, filtered and concentrated to dryness. The crude residue was chromatographed on silica gel using 20% EtOAc in hexanes as the eluant to obtain the title compound (55).

Workup

  1. customat 0° C.
  2. temperatureThe reaction was cooled to 0° C.
  3. customcarefully quenched with saturated sodium bicarbonate
  4. extractionThe mixture was extracted (2×EtOAc)
  5. washthe organics were washed with brine
  6. dry with materialThe combined organics were then dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe crude residue was chromatographed on silica gel using 20% EtOAc in hexanes as the eluant

Sources & evidence

ORD record
ord-a7353b7755854d3e90ecc9e369043e95
Source dataset
uspto-grants-1998_08
Patent number
US05789415

Reaction notes

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