3,4-dihydro-2H-pyran → 2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran

HRID 1795672Notes

Reaction equation

HRID 1795672 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][O:9]1

Participants

3

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 779706-Bromo-1-hexanol

Product 1

HCID 1038602-[(6-bromohexyl)oxy]tetrahydro-2H-pyranYield 91.1%

Procedure

197.8 g (1.09 mol) of 6-bromo-1-hexanol was put in a 500-ml reactor and was cooled to 5° C. or below. 102.1 g (1.21 mol) of dihydropyran was dropped thereto at a temperature of not higher than 10° C. After the dropping was finished, the mixture was returned to room temperature and stirred for one hour. Residue obtained as a result of the reaction was subjected to purification by silicagel column with use of hexane/diisopropyl ether (IPE)=5/1, whereby 263.4 g of 6-bromo-1-(tetrahydropyranyloxy)hexane was obtained. The yield of the same was 90.9%. The reaction of the step 1 is expressed by a formula (12) shown below: BrCH26OH→BrCH26OTHP  (12) Step 2: Synthesis of N-[6-(tetrahydropyranyloxy)hexyl]pyrrole

Workup

  1. temperaturewas cooled to 5° C. or below
  2. customhigher than 10° C
  3. customwas returned to room temperature
  4. customResidue obtained as
  5. customa result of the reaction
  6. customwas subjected to purification by silicagel column with use of hexane/diisopropyl ether (IPE)=5/1

Sources & evidence

ORD record
ord-68f3e63662ab436581ccf5f793e2e489
Source dataset
uspto-grants-2006_04
Patent number
US07027327B2

Reaction notes

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