3,4-dihydro-2H-pyran → 2-(5-Bromopentyloxy)tetrahydro-2H-pyran

HRID 1817674Notes

Reaction equation

HRID 1817674 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl.CCOCC>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][O:8]1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 1187091-Pentanol, 5-bromo-HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 27869332-(5-Bromopentyloxy)tetrahydro-2H-pyran

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

5-bromopentanol (8 g) was dissolved in dichloromethane (100 mL) and was chilled in an ice bath. Dihydropyran (9 g) was added dropwise followed by p-Toluene sulfonic acid monohydrate (1 g). The mixture was allowed to slowly warm to room temperature and stirred for 18 hours. The mixture was diluted with 200 mL ether, washed with 10% NaOH (100 mL) and dried over MgSO4 to give the title compound. δC (CDCl3, 62.9 MHz): 19.7, 25.0, 25.5, 28.9, 30.7, 32.6, 33.7, 62.4, 67.2 and 89.9.

Workup

  1. temperaturewas chilled in an ice bath
  2. washwashed with 10% NaOH (100 mL)
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-eb1a844e1c754938aead90c3d39aa049
Source dataset
uspto-grants-2009_10
Patent number
US07598289B2

Reaction notes

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