Triethylamine → 8-(4,5,6,7-Tetramethoxyindan-2-yl)octyl methanesulfonate

HRID 2268472Notes

Reaction equation

HRID 2268472 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]([O:16][CH3:17])=[C:8]2[C:4]=1[CH2:5][CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])[CH2:7]2.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36].C(=O)(O)[O-].[Na+]>C(#N)C>[CH3:34][S:35]([O:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH:6]1[CH2:7][C:8]2[C:4](=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]=2[O:16][CH3:17])[CH2:5]1)(=[O:37])=[O:36]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 18348590HCID 18348590, compound

Product 1

HCID 183485438-(4,5,6,7-Tetramethoxyindan-2-yl)octyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 8-(4,5,6,7-tetramethoxyindan-2-yl)octanol (1.95 g) and triethylamine (1.11 ml) in acetonitrile (20 ml) was dropwise added methanesufonyl chloride (0.494 ml) with cooling with ice. After the stirring was continued for 15 min, saturated aqueous sodium bicarbonate was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride, and dried. The solvent was removed in vacuo to yield the entitled compound (2.36 g) as an oil.

Workup

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

Sources & evidence

ORD record
ord-e539bf0e263349e087b4bd0d2e3e25f7
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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