Triethylamine → HCID 86663207, compound

HRID 920461Notes

Reaction equation

HRID 920461 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[C:3]=1[CH2:11][C@H:12](O)[CH3:13].CCN(CC)CC.[CH3:22][S:23](Cl)(=[O:25])=[O:24].C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:9][C:5]1[CH:6]=[C:7]([F:8])[C:2]([F:1])=[C:3]([CH2:11][C@H:12]([S:23]([CH3:22])(=[O:25])=[O:24])[CH3:13])[C:4]=1[F:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 86663206HCID 86663206, compound

Product 1

HCID 86663207HCID 86663207, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2R)-1-(2,3,5,6-tetrafluorophenyl)-propan-2-ol (E-1) (1.9 g, 9.13 mmol) and Et3N (0.85 mL, 10.95 mmol) in 40 mL anhydrous DCM was cooled in ice-water bath. Then methylsulfonyl chloride (0.85 mL, 10.95 mmol) was added slowly and the mixture was stirred for 30 min at rt. And then, saturated NaHCO3 solution (10 mL) was added to the solution and extracted with DCM, dried over anhydrous MgSO4 and concentrated, and crystallized with DCM/hexane to give white solid (2.58 g, 99%). MS (ESI) m/z 309.0 [M+Na]+, 1H NMR (CDCl3, 500 MHz) δ 7.02 (m, 1H), 5.04 (m, 1H), 3.14˜3.07 (m, 2H), 2.90 (s, 3H), 1.49 (d, J=6.0 Hz, 3H).

Workup

  1. extractionextracted with DCM
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated
  4. customcrystallized with DCM/hexane

Sources & evidence

ORD record
ord-e252bee00026477e8759debe63a01377
Source dataset
uspto-grants-2016_03
Patent number
US09273055B2

Reaction notes

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