3,4-dihydro-2H-pyran → HCID 89560017, compound

HRID 590399Notes

Reaction equation

HRID 590399 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH:10]=1)[C:8]#[N:9].[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[Cl:34]CCl.C1[CH2:41][O:40]CC1>>[Cl:34][C:6]1[CH:5]=[C:4]([CH2:41][O:40][CH:16]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[C:3]([O:2][CH3:1])=[CH:10][C:7]=1[C:8]#[N:9]

Participants

5

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 737123-Methoxybenzonitrile2×HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 21919333Tetrahydrofurane dichloromethane

Product 1

HCID 89560017HCID 89560017, compound

Procedure

To a solution of 2-chloro-4-hydroxymethyl)-5-methoxybenzonitrile (Intermediate 55; 800 mg, 4.05 mmol) in dichloromethane/THF (28 mL/12 mL) was added under nitrogen atmosphere 3,4-dihydro-2H-pyran (0.444 mL, 4.86 mmol) and pyridinium p-toluene sulfonate (100 mg, 0.4 mmol). The reaction mixture was stirred for 48 hours at room temperature. The solvent was removed under reduced pressure and the crude obtained was partitioned between ether and water. The organic layer was dried, filtered and the solvent removed giving a crude which was purified over silica gel eluting with Chloroform/Hexane (100/0 to 0/100) to give the title compound an oil (1.1 g, 98%) LRMS (m/z): 282 (M+1)+

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude obtained
  3. customwas partitioned between ether and water
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. customthe solvent removed
  7. customgiving a crude which
  8. customwas purified over silica gel eluting with Chloroform/Hexane (100/0 to 0/100)

Sources & evidence

ORD record
ord-57cddc9bb24745f9bf25dc6abf41d036
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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