Ethylene Oxide → 2-(6-methoxynaphthalen-2-yl)ethanol

HRID 1053789Notes

Reaction equation

HRID 1053789 reaction equation
C([Li])(C)(C)C.Br[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[CH:8]=1.[CH2:19]1[O:21][CH2:20]1.[NH4+].[Cl-]>C1COCC1.CCOCC>[CH3:18][O:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:19][CH2:20][OH:21])[CH:16]=[CH:15]2

Participants

7

Reactant 4

HCID 6354Ethylene OxideHCID 25517Ammonium ChlorideHCID 787862-Bromo-6-methoxynaphthaleneHCID 178418306HCID 178418306, compound

Product 1

HCID 2316102-(6-methoxynaphthalen-2-yl)ethanolYield 53%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

tert-Butyllithium (5.2 mL, 8.84 mmol, 1.7 M/pentane) was added to a −78° C. solution of 2-bromo-6-methoxynaphthalene (1.0471 g, 4.42 mmol) in THF (10 mL)/ether (10 mL). After 30 minutes, a solution of ethylene oxide in THF (2 mL, 23 mmol, 0.5 g/mL) was added and the reaction was allowed to warm to room temperature. After overnight stirring, 30 mL saturated NH4Cl solution was added and the resulting mixture was extracted with ethyl acetate (3×30 mL). The combined organic solution was then dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (ethyl acetate/hexanes) gave the title compound (478 mg, 53%).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (3×30 mL)
  2. dry with materialThe combined organic solution was then dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by flash chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b64edfb455f948ada4fcec5d61835174
Source dataset
uspto-grants-2016_07
Patent number
US09394273B2

Reaction notes

Loading…