p-Toluenesulfonic acid → 2-[2-(2-{2-[(2-Bromobenzyl)oxy]ethoxy}ethoxy)ethoxy]tetra hydro-2H-pyran

HRID 1797287Notes

Reaction equation

HRID 1797287 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH:12]1[CH2:17]CCCO1.[O:22]1[CH:27]=[CH:26][CH2:25][CH2:24][CH2:23]1.C1(C)C=CC(S(O)(=O)=[O:35])=CC=1>C1COCC1>[Br:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:17][O:35][CH:27]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 99469012-(2-(2-((2-Bromobenzyl)oxy)ethoxy)ethoxy)tetrahydro-2H-pyran

Product 1

HCID 101579922-[2-(2-{2-[(2-Bromobenzyl)oxy]ethoxy}ethoxy)ethoxy]tetra hydro-2H-pyran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound was prepared and worked up as described in the preparation of compound 420. Starting compounds were compound 416 (2.82 g, 8.9 mmol) in 6 mL dry THF, 3,4-dihydro-2H-pyran (0.89 mL, 9.8 mmol) and p-toluenesulfonic acid (37 mg, 0.19 mmol). The crude product was purified by flash chromatography using EtOAc/petroleum ether 1:3 as the eluent to afford the title compound as a pale yellow oil.

Workup

  1. customThe compound was prepared
  2. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-c848aedcda8a4b67ab099c4082de7809
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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