Ammonia → (1-Oxo-2,3-dihydro-1h-inden-5-yl)methyl methanesulfonate

HRID 2252264Notes

Reaction equation

HRID 2252264 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].N>O1CCCC1.O>[CH3:20][S:21]([O:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2)(=[O:23])=[O:22]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 691985325-(Hydroxymethyl)-2,3-dihydro-1H-inden-1-one

Product 1

HCID 85997625(1-Oxo-2,3-dihydro-1h-inden-5-yl)methyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of Example 332C (3.8 g, 23.6 mmol) and triethylamine (4.3 mL, 30.7 mmol) in tetrahydrofuran (50 mL) was added methanesulfonyl chloride (2.2 mL, 28.3 mmol) dropwise at about 0° C. After about 30 min stirring at about 0° C., the reaction mixture was diluted with water and was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), filtered and evaporated under reduced pressure to give the above intermediate. MS (DCI/NH3): m/z 258 (M+NH4)+.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give the above intermediate

Sources & evidence

ORD record
ord-6ea6c9cf8bcd4b9784b649edc9b3d2c8
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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