3,4-dihydro-2H-pyran → 2H-Pyran, 2-[(12-bromododecyl)oxy]tetrahydro-

HRID 1460996Notes

Reaction equation

HRID 1460996 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14].[O:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1>CCCCCC>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][O:15]1

Participants

4

Reactant 2

HCID 80803,4-dihydro-2H-pyran2×HCID 13789512-Bromo-1-dodecanol

Product 1

HCID 110785922H-Pyran, 2-[(12-bromododecyl)oxy]tetrahydro-Yield 118.9%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

12-Bromo-dodecan-1-ol (5.12 g, 19.3 mmol) was added to a vigorously stirred solution of dihydropyran (2.1 mL, 23.2 mmol) and Amberlyst HI5 (0.25 g, Aldrich D10,620-8) in hexane (100 mL). After 3 hours dihydropyran (2.1 mL) was added and the solution stirred for a further 15 hours. The mixture was then filtered, and the filtrate concentrated in vacuo and chromatographed graphed on silica gel, eluting with 2% ethyl acetate in hexane to give the title compound, (a), 8.02 g (75%), as an oil.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customchromatographed
  4. washeluting with 2% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3cc9204c62ce4b32bf7c5f7e11f22e5c
Source dataset
uspto-grants-1991_12
Patent number
US05073565

Reaction notes

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