2,3,5,6-Tetrafluoro-4-(2-propyn-1-yl)benzyl Alcohol → 4-propargyl-2,3,5,6-tetrafluorobenzyl (1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylate

HRID 1444840Notes

Reaction equation

HRID 1444840 reaction equation
[CH2:1]([C:4]1[C:11]([F:12])=[C:10]([F:13])[C:7]([CH2:8][OH:9])=[C:6]([F:14])[C:5]=1[F:15])[C:2]#[CH:3].[C:16]([C:18]([CH3:28])=[CH:19][C@@H:20]1[C@@H:22]([C:23](O)=[O:24])[C:21]1([CH3:27])[CH3:26])#[N:17]>CN(C)C1C=CN=CC=1.ClCCl>[C:16]([C:18]([CH3:28])=[CH:19][C@@H:20]1[C@@H:22]([C:23]([O:9][CH2:8][C:7]2[C:6]([F:14])=[C:5]([F:15])[C:4]([CH2:1][C:2]#[CH:3])=[C:11]([F:12])[C:10]=2[F:13])=[O:24])[C:21]1([CH3:27])[CH3:26])#[N:17]

Participants

5

Reactant 2

HCID 114359092,3,5,6-Tetrafluoro-4-(2-propyn-1-yl)benzyl AlcoholHCID 66664531(1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid

Product 1

HCID 866322664-propargyl-2,3,5,6-tetrafluorobenzyl (1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylateYield 74.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Under nitrogen atmosphere, to a mixture of 0.20 g of 4-propargyl-2,3,5,6-tetrafluorobenzyl alcohol, 0.17 g of (1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid, 0.022 g of 4-dimethylaminopyridine in 7 ml of dichloromethane was added 0.21 g of N,N-dicyclohexylcarbodiimide, and the mixture was stirred at room temperature for three hours. Then, the reaction mixture was filtrated, and the filtrate was concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.26 g of 4-propargyl-2,3,5,6-tetrafluorobenzyl (1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylate (hereinafter, referred to as the present compound (A)) represented by the formula (A):

Workup

  1. filtrationThen, the reaction mixture was filtrated
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1450402467174ce2b8d3f8bdd67df692
Source dataset
uspto-grants-2010_02
Patent number
US07662988B2

Reaction notes

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