Hexane → HCID 13973552, compound

HRID 1607364Notes

Reaction equation

HRID 1607364 reaction equation
[CH3:1][C:2]1([CH3:31])[CH:4]([CH:5]([OH:13])[C:6]([Cl:12])([Cl:11])[C:7]([F:10])([F:9])[F:8])[CH:3]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]=1[CH3:30])=[O:15].[CH3:32][S:33](Cl)(=[O:35])=[O:34].C(N(CC)CC)C.CCCCCC>C(OCC)C>[CH3:1][C:2]1([CH3:31])[CH:4]([CH:5]([O:13][S:33]([CH3:32])(=[O:35])=[O:34])[C:6]([Cl:11])([Cl:12])[C:7]([F:8])([F:10])[F:9])[CH:3]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:19]=1[CH3:30])=[O:15]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13933697(2-Methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(1-hydroxyl-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate

Product 1

HCID 13973552HCID 13973552, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 406 mg (0.855 mmol) of (2-methyl-3phenylphenyl)methyl 2,2-dimethyl-3-(1-hydroxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate obtained in Example 3, in 2 ml of diethyl ether, 0.079 ml (1.0 mmol) of methanesulfonyl chloride and 0.143 ml (1.0 mmol) of triethylamine, were added, and the mixture was stirred at room temperature for 1 hour. After an addition of 5 ml of hexane to the mixture, the precipitated inorganic salt was filtered off, and the filtrate was concentrated under reduced pressure. The product was purified by thin layer chromatography (silica gel, dichloromethane/hexane=1/1) to obtain 458 mg of (2-methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(1-methanesulfonyloxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate as a colorless oily substance.

Workup

  1. filtrationthe precipitated inorganic salt was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe product was purified by thin layer chromatography (silica gel, dichloromethane/hexane=1/1)

Sources & evidence

ORD record
ord-6831e6e984d94df79c78444fe3020728
Source dataset
uspto-grants-1989_09
Patent number
US04864052

Reaction notes

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