Triethylamine → 2-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl methanesulfonate

HRID 2268493Notes

Reaction equation

HRID 2268493 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][OH:16])[CH2:12][CH2:13][C:7]=2[C:6]([O:17][CH3:18])=[C:5]([O:19][CH3:20])[C:4]=1[O:21][CH3:22].C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32].C(=O)(O)[O-].[Na+]>C(#N)C>[CH3:30][S:31]([O:16][CH2:15][CH2:14][CH:11]1[CH2:12][CH2:13][C:7]2[C:6]([O:17][CH3:18])=[C:5]([O:19][CH3:20])[C:4]([O:21][CH3:22])=[C:3]([O:2][CH3:1])[C:8]=2[CH2:9][CH2:10]1)(=[O:33])=[O:32]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 183486172-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethanol

Product 1

HCID 183485372-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethanol (2.50 g) and triethylamine (1.68 ml) in acetonitrile (50 ml) was dropwise added methanesufonyl chloride (0.750 ml) with cooling with ice. After the reaction mixture was stirred for 15 min, saturated aqueous sodium bicarbonate was added to the solution with cooling with ice, which was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, water, saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride, and dried. The solvent was removed in vacuo to yield the entitled compound (3.12 g) as an oil.

Workup

  1. temperaturewith cooling with ice
  2. temperaturewith cooling with ice, which
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with 1N hydrochloric acid, water, saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride
  5. customdried
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5131699bce744640abc1975772b825f3
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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