2-Phenylethanol → HCID 66875136, compound

HRID 1799652Notes

Reaction equation

HRID 1799652 reaction equation
[H-].[Na+].[C:3]1([CH2:9][CH2:10][OH:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1>O1CCCC1.CN(C)C=O>[CH2:10]([O:11][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1)[CH2:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 60542-PhenylethanolHCID 24758Sodium hydrideHCID 109467299-Tetrahydropyranyloxy-1-bromononane

Product 1

HCID 66875136HCID 66875136, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 264 mg, 6.6 mmol) was added at 0° C. to a solution of 2-phenylethanol (807 mg, 6.61 mmol) in tetrahydrofuran (8.6 mL) and N,N-dimethylformamide (3.4 mL), then after 1 h a solution of 2-(9-bromo-nonyloxy)-tetrahydro-pyran (2.44 g, 7.93 mmol) in N,N-dimethylformamide (1.5 mL) was added dropwise. The solution was allowed to reach room temperature over 16 h, then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient) produced 2-(9-phenethyloxy-nonyloxy)-tetrahydro-pyran (898 mg, 39%). Colorless oil, m/e=366.2 ([M+NH4]+).

Workup

  1. custompartitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-60e7ad4602dc4ed2bb4fd615dd19f689
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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