p-Toluenesulfonic acid → 2-{3-[(2-Bromobenzyl)oxy]propoxy}tetrahydro-2H-pyran

HRID 1797291Notes

Reaction equation

HRID 1797291 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]OCCOC1CCCCO1.[O:22]1[CH:27]=[CH:26][CH2:25][CH2:24][CH2:23]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C[O:42][CH2:41]C1>>[Br:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][O:5][CH2:6][CH2:7][CH2:41][O:42][CH:27]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1

Participants

5

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8028TetrahydrofuranHCID 80803,4-dihydro-2H-pyranHCID 99469012-(2-(2-((2-Bromobenzyl)oxy)ethoxy)ethoxy)tetrahydro-2H-pyran

Product 1

HCID 102683722-{3-[(2-Bromobenzyl)oxy]propoxy}tetrahydro-2H-pyran

Procedure

The reaction and work up was conducted as described in the preparation of compound 420. Starting compounds were compound 424 (2.41 g, 9.8 mmol) in 7 mL dry THF, 3,4-dihydro-2H-pyran (0.99 mL, 10.8 mmol) and p-toluenesulfonic acid (37 mg, 0.19 mmol). The crude product was purified by flash chromatography using EtOAc/petroleum ether 1:4 as the eluent to afford the title compound as a pale yellow oil.

Workup

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

Sources & evidence

ORD record
ord-19782a6c569a422888a796a01a126cbb
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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