Triethylamine → HCID 86663207, compound

HRID 69335Notes

Reaction equation

HRID 69335 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, =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-d04b4bbef90d4aaf8d3d9ebcdc0d63d4
Source dataset
uspto-grants-2014_09
Patent number
US08822500B2

Reaction notes

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