Sodium Hydroxide → HCID 23695524, compound

HRID 2107131Notes

Reaction equation

HRID 2107131 reaction equation
C[O:2][C:3]([C:5]1([C:8]([F:23])([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+:25]>C(O)C.O>[Na+:25].[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]([C:5]2([C:3]([O-:4])=[O:2])[CH2:7][O:6]2)([F:22])[F:23])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14348917HCID 14348917, compound

Product 1

HCID 23695524HCID 23695524, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 348 mg (1 mmol) of 2-[6-(4-chlorophenoxy)-1,1-difluorohexyl]-2-oxiranecarboxylic acid methyl ester of Example 7 in 10 ml of 95% ethanol is treated with a solution of 40 mg (1 mmol) of sodium hydroxide in 5 ml of water. The solution is stirred at room temperature for 3 hours and is then rotoevaporated. The obtained solid is triturated two times with ethyl ether and the solvent is removed to give 289 mg (77.1%) of the title compound: m.p. 140°-153° C.; IR (KBr) 1645, 1618 cm-1 ; NMR (d6 -DMSO) δ 1.46 (4H, m), 1.73 (2H, p, J=7 Hz), 2.42 (2H, m), 2.70 (1H, d, J=7 Hz), 2.76 (1H, d, J=7 Hz), 3.98 (2H, t, J=7 Hz), 7.00 (2H, d, J=10 Hz) and 7.36 (2H, d, J=10 Hz).

Workup

  1. customThe obtained solid is triturated two times with ethyl ether
  2. customthe solvent is removed

Sources & evidence

ORD record
ord-d53191b7cab94e8ba406b69120680c5e
Source dataset
uspto-grants-1990_06
Patent number
US04933365

Reaction notes

Loading…