3,4-dihydro-2H-pyran → HCID 22054525, compound

HRID 1743924Notes

Reaction equation

HRID 1743924 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:13][OH:14])=[C:9]([CH3:12])[CH:10]=2)[N:5]=[C:4]([CH3:15])[CH:3]=1.[O:16]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl.C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:13][O:14][CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21][O:16]3)=[C:9]([CH3:12])[CH:10]=2)[N:5]=[C:4]([CH3:15])[CH:3]=1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 22054471HCID 22054471, compound

Product 1

HCID 22054525HCID 22054525, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (4-chloro-2,6-dimethyl-quinolin-7-yl)-methanol (example 59c, 300 mg, 1.35 mmol), 3,4-dihydro-2H-pyran (342 mg, 4.06 mmol), and pyridinium toluene-4-sulfonate (374 mg, 1.49 mg) in dichloromethane (3 mL) and toluene (3 mL) was stirred at r.t. for 3 d, then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), and evaporated. Flash chromatography (SiO2, hexane/ethyl acetate gradient) afforded the title compound (243 mg, 59%). White solid, ISP-MS: m/e=306.3 ([M+H]+).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-6992c8823778448180f50ab20ff63716
Source dataset
uspto-grants-2006_03
Patent number
US07012073B2

Reaction notes

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