3,4-dihydro-2H-pyran → 11-Bromo-1-tetrahydropyranyloxyundecane

HRID 601785Notes

Reaction equation

HRID 601785 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1.[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30].[O:31]1[CH:36]=[CH:35][CH2:34][CH2:33][CH2:32]1>>[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH:32]1[CH2:33][CH2:34][CH2:35][CH2:36][O:31]1

Participants

4

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 7416311-Bromo-1-undecanolHCID 161440Pyridine 4-methylbenzene-1-sulfonate

Product 1

HCID 1141638811-Bromo-1-tetrahydropyranyloxyundecane

Procedure

Pyridine toluene 4-sulphonate (1,0 g, 4,0 mmol) and 11-Bromo-1-undecanol (10,0 g, 400 mmol) were dissolved in dry CH2CH2 (200 ml) at ambient temperature, and 3,4-dihydro-2H-pyrane (5,0 g, 60 mmol) was added. The reaction mixture was stirred overnight. The crude product was purified by flash chromatography on silica gel eluted with CH2Cl2. The yield of 11-Bromo-1(tetrahydro-2-pyranyloxy)undecane was 10,7 g (80%).

Workup

  1. customThe crude product was purified by flash chromatography on silica gel
  2. washeluted with CH2Cl2

Sources & evidence

ORD record
ord-91f440436d314e2a95be3ce5b9c82c03
Source dataset
uspto-grants-2011_03
Patent number
US07902399B2

Reaction notes

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