Triethylamine → HCID 58987887, compound

HRID 1363988Notes

Reaction equation

HRID 1363988 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[C:6]([O:13][CH3:14])=[C:5]([CH3:15])[C:4]=1[CH2:16][CH2:17][CH2:18][OH:19].C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[CH3:27][S:28]([O:19][CH2:18][CH2:17][CH2:16][C:4]1[C:3]([O:2][CH3:1])=[C:8]([O:9][CH3:10])[C:7]([O:11][CH3:12])=[C:6]([O:13][CH3:14])[C:5]=1[CH3:15])(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13389493HCID 13389493, compound

Product 1

HCID 58987887HCID 58987887, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 3 (3.88 g, 15 mmol) and triethylamine (3.0 g, 30 mmol, 4.2 mL) in CH2Cl2 (50 mL) was stirred at room temperature for 10 mins. Methanesulfonyl chloride (1.8 g, 1.20 mL, 15.75 mmol) in CH2Cl2 (50 mL) was added dropwise over 20 mins and the reaction mixture stirred at room temperature for 1 hr. The mixture was then diluted with CH2Cl2 (50 mL) and the organic layer was washed with H2O (5×100 mL), 10% aqueous NaHCO3 (100 mL), dried (MgSO4), filtered and the solvent removed in vacuo by rotary evaporation to afford 1-(3-methanesulfonyloxypropyl)-2-methyl-3,4,5,6-tetramethoxybenzene (4) as a liquid (4.8 g, 95%). 1H NMR δ4.277 (2H, t, J=7.0 Hz, —CH2—O—SO2-Me), 3.91, 3.89, 3.82, 3.78 (12H, s, OMe), 3.03 (3H, s, —O—SO2-Me), 2.70 (2H, t, J=7.0 Hz, Ar—CH2—), 2.17 (3H, s, Ar-Me), 1.9 (2H, m, —CH2—) ppm.

Workup

  1. washthe organic layer was washed with H2O (5×100 mL), 10% aqueous NaHCO3 (100 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent removed in vacuo by rotary evaporation

Sources & evidence

ORD record
ord-0e8cb61eb8a8496796a2988cd75e92cb
Source dataset
uspto-grants-2011_02
Patent number
US07888335B2

Reaction notes

Loading…