Water → HCID 20510023, compound

HRID 1758271Notes

Reaction equation

HRID 1758271 reaction equation
S(Cl)([Cl:3])=O.O[CH:6]([C:10]1[CH:11]=[CH:12][C:13]2[O:17][CH2:16][CH2:15][C:14]=2[CH:18]=1)[CH:7]([CH3:9])[CH3:8].O>ClCCl>[Cl:3][CH:6]([C:10]1[CH:11]=[CH:12][C:13]2[O:17][CH2:16][CH2:15][C:14]=2[CH:18]=1)[CH:7]([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 20510018HCID 20510018, compound

Product 1

HCID 20510023HCID 20510023, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (2.02 cm3, 0.265 mol) was added dropwise to a stirred solution of 2,3-dihydro-5-(1-hydroxy-2-methyl-1-propyl)benzofuran (5.10 g, 0.0265 mol) pyridine (2.16 cm3, 0.0265 mol) in dichloromethane (45 cm3) at 0°-5° C., and the mixture was heated to reflux for 3 hr. The mixture was poured into water and separated. The organic layer was washed with hydrochloric acid (2 N, 20 cm3), water, dried (Na2SO4), filtered and the solvent was removed. The residue was subjected to column chromatography on silica using toluene as the eluant. The appropriate fractions were combined and the solvent was removed to give 5-(1-chloro-2-methyl-1-propyl)-2,3-dihydrobenzofuran. (5.43 g, 0.028 mol, 97.2%) RF 0.68.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hr
  3. customseparated
  4. washThe organic layer was washed with hydrochloric acid (2 N, 20 cm3), water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was removed
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-57433c975649415c8fbf9e5e03119309
Source dataset
uspto-grants-1983_02
Patent number
US04372970

Reaction notes

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