3-Hydroxybenzaldehyde → tetrahydro-2-(2-(4-(3-formylphenoxy)phenoxy)ethoxy)-2H-pyran

HRID 892863Notes

Reaction equation

HRID 892863 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].Br[C:11]1[CH:26]=[CH:25][C:14]([O:15][CH2:16][CH2:17][O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.[Cu]>[CH:5]([C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][C:11]1[CH:26]=[CH:25][C:14]([O:15][CH2:16][CH2:17][O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)=[CH:13][CH:12]=1)=[O:6]

Participants

6

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 128104732-[2-(4-Bromophenoxy)ethoxy]tetrahydro-2H-pyran

Product 1

HCID 19894145tetrahydro-2-(2-(4-(3-formylphenoxy)phenoxy)ethoxy)-2H-pyranYield 87%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1049PyridineSolvent

Procedure

A solution of 3-hydroxybenzaldehyde (1.27 g, 10.4 mmol), tetrahydro-2-(2-(4-bromophenoxy)ethoxy)-2H-pyran (6.26 g, 20.8 mmol), potassium carbonate (2.23 g, 16.12 mmol) and copper (330 mg, 5.2 mmol) in pyridine (10 mL) was refluxed for 5 days. It was then cooled to r.t., filtered through Celite, diluted with ethylacetate (50 mL), and washed with H2O (3×40 mL). The organic was dried with MgSO4 and concentrated. The resulting residue was chromatographed (silica gel, ether:hexanes, 2:3) to afford tetrahydro-2-(2-(4-(3-formylphenoxy)phenoxy)ethoxy)-2H-pyran (3.09 g, 87%) as a pale yellow oil.

Workup

  1. filtrationfiltered through Celite
  2. additiondiluted with ethylacetate (50 mL)
  3. washwashed with H2O (3×40 mL)
  4. dry with materialThe organic was dried with MgSO4
  5. concentrationconcentrated
  6. customThe resulting residue was chromatographed (silica gel, ether:hexanes, 2:3)

Sources & evidence

ORD record
ord-d01b8bd852ad45b992ab0eacafaedce7
Source dataset
uspto-grants-1992_06
Patent number
US05120752

Reaction notes

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