Triethylamine → HCID 19036538, compound

HRID 264506Notes

Reaction equation

HRID 264506 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][C:7]1[CH:15]=[C:14]2[C:10]([CH2:11][CH2:12][C:13]2=[O:16])=[CH:9][CH:8]=1.C(N(CC)CC)C>ClCCl>[S:2]([O:6][C:7]1[CH:15]=[C:14]2[C:10]([CH2:11][CH2:12][C:13]2=[O:16])=[CH:9][CH:8]=1)([CH3:1])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 70206596-Hydroxy-1-indanone

Product 1

HCID 19036538HCID 19036538, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

12.6 ml of methanesulfonyl chloride were added dropwise while stirring to a solution, cooled to 0°, of 12.0 g of 6-hydroxy-1-indanone and 45.2 ml of triethylamine in 350 ml of dichloro-methane and the solution was stirred at this temperature for an additional 1.5 hours. The reaction mixture was subsequently diluted with 200 ml of dichloromethane, washed twice with 150 ml of saturated sodium hydrogen carbonate solution each time an the combined aqueous phases were extracted once with 100 ml of dichloromethane. The combined organic phases were washed with 200 ml of saturated sodium chloride solution, dried over magnesium sulfate and evaporated in a vacuum. 18.3 g (99%) of 6-mesyloxy-1-indanone were obtained as a brown solid which was used directly in the next reaction.

Workup

  1. stirringthe solution was stirred at this temperature for an additional 1.5 hours
  2. washwashed twice with 150 ml of saturated sodium hydrogen carbonate solution each time an the combined aqueous phases
  3. extractionwere extracted once with 100 ml of dichloromethane
  4. washThe combined organic phases were washed with 200 ml of saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in a vacuum

Sources & evidence

ORD record
ord-e8994b9f4b99499a86eb94426bb7cc3f
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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