4-Toluenesulfonyl chloride → HCID 89814515, compound

HRID 715121Notes

Reaction equation

HRID 715121 reaction equation
[F:1][C:2]([F:8])([CH3:7])[CH2:3][CH2:4][CH2:5][OH:6].[S:9](Cl)([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:16][C:15]1[CH:17]=[CH:18][C:12]([S:9]([O:6][CH2:5][CH2:4][CH2:3][C:2]([F:8])([F:1])[CH3:7])(=[O:11])=[O:10])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 541480841455037-30-5

Product 1

HCID 89814515HCID 89814515, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Treat a solution of 4,4-difluoropentan-1-ol (5 g, 40.3 mmol) and TsCl (8.4 g, 44.3 mmol) in DCM (80 mL) with TEA (6.1 g, 60 mmol) and DMAP (0.5 g, 4 mmol) and stir at RT overnight. Wash the mixture successively with 2M HCl, satd. NaHCO3, then brine, dry over Na2SO4, concentrate and purify by silica gel chromatography (EtOAc/Pet ether) to give the title compound (7.1 g, 63%). 1H NMR (400 MHz, CDCl3): δ 7.80 (d, J=8.0 Hz, 2H), 7.36 (d, J=8.0 Hz, 2H), 4.08 (t, J=5.6 Hz, 2H), 2.47 (s, 3H), 1.94-1.84 (m, 4H), 1.57 (t, J=18.4 Hz, 3H).

Workup

  1. washWash the mixture successively with 2M HCl
  2. dry with materialNaHCO3, then brine, dry over Na2SO4
  3. concentrationconcentrate
  4. custompurify by silica gel chromatography (EtOAc/Pet ether)

Sources & evidence

ORD record
ord-2a680886353443108271830b092cbafb
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

Loading…