3,4-dihydro-2H-pyran → 1-(4'-(2-Tetrahydropyranyloxy)phenyl)-3-bromopropane

HRID 2227106Notes

Reaction equation

HRID 2227106 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][Br:11])=[CH:4][CH:3]=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.P(Cl)(Cl)(Cl)=O>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][Br:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 11430Potassium CarbonateHCID 148170364-(3-Bromopropyl)phenol

Product 1

HCID 184717901-(4'-(2-Tetrahydropyranyloxy)phenyl)-3-bromopropane

Reagents, catalysts & solvents 2

HCID 24813Phosphorus oxychlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(4′-hydroxyphenyl)-3-bromopropane 3B (3.56 g) in dichloromethane (11 mL) is added dihydropyran (2.3 mL). The reaction mixture is cooled to 0° C., and three drops of phosphorus oxychloride are added. The reaction mixture is stirred in the ice bath for a further two hours, then gradually allowed to warm to room temperature, where it is allowed to stir overnight. To the reaction mixture is then added potassium carbonate (3 g), and the reaction mixture is stirred an additional hour. The solid is then filtered out, and the solvents and residual DHP is removed in vacuo.

Workup

  1. temperatureto warm to room temperature
  2. filtrationThe solid is then filtered out
  3. customthe solvents and residual DHP is removed in vacuo

Sources & evidence

ORD record
ord-3936bb0374a549fba4004c4ecbb16f12
Source dataset
uspto-grants-2002_07
Patent number
US06413448B1

Reaction notes

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