Triethylamine → 1,2-Methylenedioxy-4-[3-mesyloxypropyl]benzene

HRID 892999Notes

Reaction equation

HRID 892999 reaction equation
[CH2:1]1[O:13][C:4]2[CH:5]=[C:6]([CH2:9][CH2:10][CH2:11][OH:12])[CH:7]=[CH:8][C:3]=2[O:2]1.[CH3:14][S:15](Cl)(=[O:17])=[O:16].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]1[O:13][C:4]2[CH:5]=[C:6]([CH2:9][CH2:10][CH2:11][O:12][S:15]([CH3:14])(=[O:17])=[O:16])[CH:7]=[CH:8][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 110304141,3-Benzodioxole-5-propanol

Product 1

HCID 198946281,2-Methylenedioxy-4-[3-mesyloxypropyl]benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,2-methylenedioxy-4-[3-hydorxypropyl]benzene, (10.0 g), methanesulfonyl chloride (6.33 g, 4.28 ml) and triethylamine (5.6 g) in methylene chloride (100 ml) is stirred at 0° for 2 hr. The reaction mixture is partitioned between methylene chloride and aqueous sodium bicarbonate. The organic phase is dried over sodium sulfate and concentrated. The residue is dissolved in acetonitrile (100 ml).

Workup

  1. customThe reaction mixture is partitioned between methylene chloride and aqueous sodium bicarbonate
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. concentrationconcentrated
  4. dissolutionThe residue is dissolved in acetonitrile (100 ml)

Sources & evidence

ORD record
ord-bdb99ad8f8a647e890dbbb52ce84a834
Source dataset
uspto-grants-1992_06
Patent number
US05120843

Reaction notes

Loading…