Methanesulfonyl chloride → HCID 70654827, compound

HRID 879109Notes

Reaction equation

HRID 879109 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2(O)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.CS(Cl)(=O)=O.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:14][CH2:13][O:12][CH2:11][CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 193886354-(3,5-Difluorophenyl)oxan-4-ol

Product 1

HCID 70654827HCID 70654827, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-(3,5-difluorophenyl)tetrahydro-2H-pyran-4-ol (1.0 equiv.) was dissolved in DCM (0.2 M) and cooled to 0° C. TEA (2.8 equiv.) was added to the solution, followed by MsCl (1.3 equiv.). The reaction was stirred at rt for 2 hrs. The solution was cooled to 0° C. and DBU (3.0 equiv.) was added. The reaction was stirred at rt for 18 hrs. The solution was concentrated and the residue was purified by SiO2 chromatography (0-100% EtOAc in Heptanes) to afford 4-(3,5-difluorophenyl)-3,6-dihydro-2H-pyran in 38% yield. 1H NMR (400 MHz, <cdcl3>) δ ppm 2.42-2.49 (m, 2H), 3.93 (t, J=5.48 Hz, 2H), 4.32 (q, J=2.74 Hz, 2H), 6.16-6.22 (m, 1H), 6.70 (tt, J=8.80, 2.35 Hz, 1H), 6.85-6.94 (m, 2H).

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. stirringThe reaction was stirred at rt for 18 hrs
  3. concentrationThe solution was concentrated
  4. customthe residue was purified by SiO2 chromatography (0-100% EtOAc in Heptanes)

Sources & evidence

ORD record
ord-298b647f27fc471bb9c5a965ae55ab80
Source dataset
uspto-grants-2015_03
Patent number
US08987457B2

Reaction notes

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