2-Dimethylaminopyridine → 2,3-Dihydro-1h-inden-2-yl methanesulfonate

HRID 450726Notes

Reaction equation

HRID 450726 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[OH:10].C(N(C(C)C)CC)(C)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].CN(C1C=CC=CN=1)C>ClCCl>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[O:10][S:21]([CH3:20])(=[O:23])=[O:22]

Participants

6

Reactant 4

HCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 779362-IndanolHCID 81531Diisopropylethylamine

Product 1

HCID 2552212,3-Dihydro-1h-inden-2-yl methanesulfonateYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Indanol (20.00 g, 149.5 mmol) and diisopropylethylamine (21.2 g, 164 mmol) was stirred in dichloromethane (300 mL) at 0° C. Methanesulfonyl chloride (18.78 g, 164 mmol) and dimethylaminopyridine (1.80 g) were added simultaneously and stirring continued at room temperature for 18 h. Solution was evaporated, partitioned between ethyl acetate and water, and the organic phase separated. This was washed with NaHCO3 (sat) and with citric acid solution (5%) and dried over MgSO4. The filtered solution was concentrated and the resultant solid recrystallized from isopropanol-EtOH (3:1) to give off-white crystals (24.6 g, 78%).

Workup

  1. customSolution was evaporated
  2. custompartitioned between ethyl acetate and water
  3. customthe organic phase separated
  4. washThis was washed with NaHCO3 (sat) and with citric acid solution (5%)
  5. dry with materialdried over MgSO4
  6. concentrationThe filtered solution was concentrated
  7. customthe resultant solid recrystallized from isopropanol-EtOH (3:1)

Sources & evidence

ORD record
ord-8a773c1aeae7433abb88a6f5b83d4413
Source dataset
uspto-grants-2013_07
Patent number
US08486984B2

Reaction notes

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