p-Toluenesulfonic acid → 2-(2-((2-Bromobenzyl)oxy)ethoxy)tetrahydro-2H-pyran

HRID 1797288Notes

Reaction equation

HRID 1797288 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]OC1CCCCO1.[O:22]1C=C[CH2:25][CH2:24][CH2:23]1.C1(C)C=CC(S(O)(=O)=O)=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][CH:9]1[CH2:10][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 98798912-(2-((2-Bromobenzyl)oxy)ethoxy)tetrahydro-2H-pyran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction and work up was conducted as described in the preparation of compound 420. Starting materials were compound 417 (8.0 g, 34.9 mmol) in 20 mL dry THF, 3,4-dihydro-2H-pyran (3.2 mL, 34.9 mmol) and p-toluenesulfonic acid (0.14 g, 0.76 mmol) and the reaction time was 4 h. The crude product was purified by flash chromatography using EtOAc/petroleum ether 1:2 as the eluent to afford the title compound as a colourless oil.

Workup

  1. customThe reaction and work
  2. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-d7373535b1aa415e9b08da7c5f3d7216
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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