Sodium Hydroxide → HCID 23695520, compound

HRID 2232626Notes

Reaction equation

HRID 2232626 reaction equation
C[O:2][C:3]([C:5]1([CH:8]([F:21])[CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:7][O:6]1)=[O:4].[OH-].[Na+:23]>C(O)C.O>[Na+:23].[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH:8]([C:5]2([C:3]([O-:4])=[O:2])[CH2:7][O:6]2)[F:21])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54007397HCID 54007397, compound

Product 1

HCID 23695520HCID 23695520, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-[5-(4-chlorophenoxy)-1-fluoropentyl]-2-oxiranecarboxylic acid methyl ester (2.53 g, 8 mmol) of Example 2 in 25 ml of absolute ethanol is treated with a solution of 320 mg (8 mmol) of sodium hydroxide in 12 ml of water. The mixture is maintained with stirring at room temperature for 2 hours and then is rotoevaporated. The obtained solid is triturated three times with ethyl ether, the solvent is removed by rotoevaporation and the solid is dried at high vacuum over phosphorus pentoxide to give 2.25 g (86.6%) of the title compound: m.p. 159°-175° C.; IR (KBr) 1630, 1608, 1490 and 1242 cm-1 ; NMR (d6 -DMSO) δ1.54 (2H, m), 1.73 (4H, m), 2.65 (1H, m), 2.73 (1H, d, J=6 Hz), 3.98 (2H, t, J=6 Hz), 5.22 (1H, ddd, JHF =48, 10, 3 Hz), 7.00 (2H, d, J=9 Hz) and 7.36 (2H, d, J=9 Hz).

Workup

  1. temperatureThe mixture is maintained
  2. customThe obtained solid is triturated three times with ethyl ether
  3. customthe solvent is removed by rotoevaporation
  4. dry with materialthe solid is dried at high vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-81cf0ac80f9c45cc9ac017fe1808fb0b
Source dataset
uspto-grants-1988_11
Patent number
US04788304

Reaction notes

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