Potassium Carbonate → 1-[2-(Tetrahydropyran-2-yloxy)ethyl]-4-(3-hydroxypropy)benzene

HRID 34409Notes

Reaction equation

HRID 34409 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13](O)=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH2:25][CH2:26][OH:27]>CC(=O)CC>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:24][CH2:25][CH2:26][OH:27])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 142087834-(2-Tetrahydropyran-2-yloxyethyl)phenol

Product 1

HCID 704201991-[2-(Tetrahydropyran-2-yloxy)ethyl]-4-(3-hydroxypropy)benzeneYield 73.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 4-(2-tetrahydropyran-2-yloxyethyl)phenol (9, 8.0 g, 36 mmoles) in 2-butanone (100 mL) were added K2CO3 (10.0 g, 72 mmoles) and 3-bromopropanol (6.5 mL, 72 mmoles). The solution was refluxed 18 hours with mechanical stirring. After cooling, the mixture was filtered and the solvent removed under reduced pressure to afford 13.0 g of crude oil. This was purified by flash chromatography on silica gel (solvent=80:20 ethyl acetate:heptane). The pure fractions were pooled and the solvent removed in vacuo to give 7.0 g of 1-[2-(tetrahydropyran-2-yloxy)ethyl]-4-(3-hydroxypropy)benzene (10). NMR (CDCl3)δppm: 7.0(q, 4H); 4.58(s, 1H)' 4.3-3.3(m, 8H); 3.06(s, 1H); 2.83(t, 2H); 1.83(m, 2H); 1.63(m, 6H). (Scheme II, Step 5.)

Workup

  1. temperatureThe solution was refluxed 18 hours with mechanical stirring
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. customthe solvent removed under reduced pressure
  5. customto afford 13.0 g of crude oil
  6. customThis was purified by flash chromatography on silica gel (solvent=80:20 ethyl acetate:heptane)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-0d3e6905d57546e0bc7c52aceb0a152e
Source dataset
uspto-grants-1988_08
Patent number
US04761420

Reaction notes

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