3,4-dihydro-2H-pyran → HCID 86636416, compound

HRID 1471488Notes

Reaction equation

HRID 1471488 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=2[CH:15]=[O:16])=[CH:4][C:3]=1[CH2:19][OH:20].[O:21]1[CH:26]=[CH:25][CH2:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[Na+].[Na+].O.C(Cl)(Cl)Cl>ClCCl.CC1(C)[C@]2(CS(O)(=O)=O)C(C[C@H]1CC2)=O>[Br:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=2[CH:15]=[O:16])=[CH:4][C:3]=1[CH2:19][O:20][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][O:21]1

Participants

7

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 10340Sodium CarbonateHCID 22418719Chloroform waterHCID 86636415HCID 86636415, compound

Product 1

HCID 86636416HCID 86636416, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 65617D-Camphorsulfonic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[4-bromo-3-(hydroxymethyl)phenoxy]-3-formylbenzonitrile (25.5 g, 76.8 mmol), 3,4-dihydro-2H-pyran (10.4 mL, 115 mmol), and dl-10-camphorsulfonic acid (356 mg, 2 mol %) in dichloromethane (300 mL) was stirred at room temperature for 2 h. Sodium carbonate (3 g) was added, and the mixture was poured into water/chloroform. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column (85:15 hexane/ethyl acetate) to give 4-[4-bromo-3-(2-tetrahydropyranyloxymethyl)phenoxy]-3-formylbenzonitrile (28.0 g, 88%).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried on anhydrous sodium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by silica gel column (85:15 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e7902be9f590493e86d3e722edc8d890
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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