2-(2-Bromoethoxy)tetrahydro-2H-pyran → 1-{3-tert-Butyl-4-methoxy-5-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl}ethanone

HRID 217733Notes

Reaction equation

HRID 217733 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:14](=[O:16])[CH3:15])[CH:8]=[C:9]([OH:13])[C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].Br[CH2:18][CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1>>[C:1]([C:5]1[CH:6]=[C:7]([C:14](=[O:16])[CH3:15])[CH:8]=[C:9]([O:13][CH2:18][CH2:19][O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[C:10]=1[O:11][CH3:12])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 581369461-(3-Tert-butyl-5-hydroxy-4-methoxyphenyl)ethanone

Product 1

HCID 581369271-{3-tert-Butyl-4-methoxy-5-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl}ethanoneYield 84.7%

Procedure

Analogously to O2.071, 1-(3-tert-butyl-5-hydroxy-4-methoxyphenyl)ethanone (O3.070; 5.0 g) was reacted with 2-(2-bromoethoxy)tetrahydropyran (5.64 g). However, the crude product was purified using silica gel (40 g cartridge, n-heptane/EA gradient of 0-50% within 60 min). 6.68 g of the title compound were obtained.

Workup

  1. customHowever, the crude product was purified
  2. customsilica gel (40 g cartridge, n-heptane/EA gradient of 0-50% within 60 min)

Sources & evidence

ORD record
ord-6166a843867c4ca18bade433f030d725
Source dataset
uspto-grants-2012_06
Patent number
US08198272B2

Reaction notes

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