Ethanol → HCID 86691239, compound

HRID 2038222Notes

Reaction equation

HRID 2038222 reaction equation
[Na].[CH3:2][CH2:3][OH:4].[F:5][C:6]1[CH:16]=[CH:15][C:9]([O:10][CH2:11][CH:12]2[CH2:14][O:13]2)=[CH:8][CH:7]=1>CCOC(C)=O>[CH2:3]([O:4][CH2:14][CH:12]([OH:13])[CH2:11][O:10][C:9]1[CH:15]=[CH:16][C:6]([F:5])=[CH:7][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 27247922-[(4-Fluorophenoxy)methyl]oxiraneHCID 5360545Sodium

Product 1

HCID 86691239HCID 86691239, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Slowly add sodium (1 g, 43.5 mmol) to absolute EtOH (80 mL) and stir the mixture at ambient temperature for 2 hours. Add 2-[(4-fluorophenoxy)methyl]oxirane (2.0 g, 11.89 mmol) in a single portion and stir for 16 hours at ambient temperature. Add 30 mL EtOAc; wash with H2O (10 mL) three times; then dry the organic layer over Na2SO4; filter; and concentrate the filtrate under reduced pressure to give the title compound (2.55 g, 86.3%) as a yellow oil. 1H NMR (300 MHz, d6-DMSO) δ 7.15 (m, 2H), 6.95 (m, 2H), 5.05 (m, 1H), 3.95 (m, 3H), 3.49 (m, 4H), 1.05 (t, 3H).

Workup

  1. washwash with H2O (10 mL) three times
  2. dry with materialthen dry the organic layer over Na2SO4
  3. filtrationfilter
  4. concentrationand concentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-44c8898919ac48f1b817ac28eac341a4
Source dataset
uspto-grants-2013_11
Patent number
US08575352B2

Reaction notes

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