Tetrahydrofuran → HCID 23695522, compound

HRID 2232658Notes

Reaction equation

HRID 2232658 reaction equation
C[O:2][C:3]([C:5]1([CH:8]([F:22])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:7][O:6]1)=[O:4].[OH-].[Na+:24].O1CCCC1>C(O)C>[Na+:24].[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][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:22])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 54555840HCID 54555840, compound

Product 1

HCID 23695522HCID 23695522, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 1.79 g (5.41 mmol) of 2-[6-(4-chlorophenoxy)-1-fluorohexyl]-2-oxiranecarboxylic acid methyl ester (isomer A) of Example 3 in 5.14 ml of absolute ethanol is added at room temperature 5.14 ml (5.14 mmol) of 1N aqueous sodium hydroxide. After 30 minutes, 4.0 ml of tetrahydrofuran is aded to achieve total dissolution and stirring is maintained for 1.25 hours. Evaporation of the solvents and trituration with pentane and isopropyl ether gives 1.46 g (79.7%) of the title compound: m.p. 112°-125° C.; IR (KBr) 1640, 1608 cm-1 ; NMR (d6 -DMSO) δ 1.47 (4H, m), 1.74 (4H, m), 2.63 (1H, dd, J=8, 3 Hz), 2.73 (1H, d, J=8 Hz), 3.98 (2H, t, J=9 Hz), 5.19 (1H, ddd, J=48, 10, 2 Hz), 6.98 (2H, d, J=8 Hz).

Workup

  1. dissolutiondissolution
  2. temperatureis maintained for 1.25 hours
  3. customEvaporation of the solvents and trituration with pentane and isopropyl ether

Sources & evidence

ORD record
ord-108524d31faa4234a7c5ab0cb7aad5c6
Source dataset
uspto-grants-1988_11
Patent number
US04788306

Reaction notes

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