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3,4-dihydro-2H-pyran → 2-[(10-Bromodecyl)oxy]tetrahydro-2H-pyran

HRID 481264
Notes
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Reaction equation

HRID 481264 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12].[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1>N1C=CC=CC=1.C[Si](OS(O[Si](C)(C)C)(=O)=O)(C)C.ClCCl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][O:13]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 1045071-Decanol, 10-bromo-

Product 1

HCID 1035432-[(10-Bromodecyl)oxy]tetrahydro-2H-pyranYield 42.8%

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 87573Silanol, trimethyl-, 1,1'-sulfateCatalyst
HCID 6344
Dichloromethane
Solvent

Procedure

A mixture of 100 g 1-bromodecan-10-ol, 2.1 g bis(trimethylsilyl)sulphate, 43 g 3,4-dihydro-2H-pyran and 500 ml dichloromethane is stirred for 6 hours at room temperature. Several drops of pyridine are added and the reaction mixture evaporated down. The residue is purified by column chromatography on silica gel using hexane/ethyl acetate (1/1 v/v) as eluent to yield 58 g of 1-bromo-10-[tetrahydropyranyloxy]decane.

Workup

  1. customthe reaction mixture evaporated down
  2. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-270d3152095d4875925be10b4e5aff8a
Source dataset
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06653499B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes