3,4-dihydro-2H-pyran → HCID 44190364, compound

HRID 1959583Notes

Reaction equation

HRID 1959583 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:19][C:20]1[CH:21]=[N:22][CH:23]=[C:24]([Cl:28])[C:25]=1[CH2:26][OH:27]>C(Cl)Cl>[Cl:19][C:20]1[CH:21]=[N:22][CH:23]=[C:24]([Cl:28])[C:25]=1[CH2:26][O:27][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 17855219(3,5-Dichloropyridin-4-yl)methanol

Product 1

HCID 44190364HCID 44190364, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Dihydropyrane (3.01 mL, 33.2 mmol) and p-toluenesulfonic acid monohydrate (5.06 g, 26.6 mmol) were added to a stirred solution of (3,5-dichloro-pyridin-4-yl)-methanol (1.97 g, 11.06 mmol) in DCM (40 mL). After stirring for 1 d at 40° C. the solvent was removed in vacuo and the residue was partitioned between DCM (50 mL) and saturated NaHCO3 solution (50 mL). After extraction of the aqueous layer with DCM (2×50 mL) the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with mixtures of hexane and EA) to give the title compound. MS (m/z): 261.9 [M+H+].

Workup

  1. customwas removed in vacuo
  2. customthe residue was partitioned between DCM (50 mL) and saturated NaHCO3 solution (50 mL)
  3. extractionAfter extraction of the aqueous layer with DCM (2×50 mL) the combined organic layers
  4. dry with materialwere dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (elution with mixtures of hexane and EA)

Sources & evidence

ORD record
ord-ffe9ea8614ec49ac911559b3150dcbc1
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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