4-Methoxy-2,3,5,6-tetrafluorobenzyl alcohol → HCID 86652079, compound

HRID 384423Notes

Reaction equation

HRID 384423 reaction equation
[CH3:1][O:2][C:3]1[C:10]([F:11])=[C:9]([F:12])[C:6]([CH2:7][OH:8])=[C:5]([F:13])[C:4]=1[F:14].[C:15]([C:17]([CH3:27])=[CH:18][C@@H:19]1[C@@H:21]([C:22](O)=[O:23])[C:20]1([CH3:26])[CH3:25])#[N:16]>CN(C)C1C=CN=CC=1.ClCCl>[C:15]([C:17]([CH3:27])=[CH:18][C@@H:19]1[C@@H:21]([C:22]([O:8][CH2:7][C:6]2[C:5]([F:13])=[C:4]([F:14])[C:3]([O:2][CH3:1])=[C:10]([F:11])[C:9]=2[F:12])=[O:23])[C:20]1([CH3:26])[CH3:25])#[N:16]

Participants

5

Reactant 2

HCID 119618954-Methoxy-2,3,5,6-tetrafluorobenzyl alcoholHCID 66664531(1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid

Product 1

HCID 86652079HCID 86652079, compoundYield 70.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, 0.49 g of N,N-dicyclohexylcarbodiimide was added to a mixture of 0.50 g of 4-methoxy-2,3,5,6-tetrafluorobenzyl alcohol, 0.43 g of (1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid, 0.087 g of 4-dimethylaminopyridine and 7 ml of anhydrous dichloromethane, and the mixture was stirred at room temperature for 3 hours. Thereafter, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 0.62 g of 4-methoxy-2,3,5,6-tetrafluorobenzyl (1R) trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylate represented by the following formula:

Workup

  1. filtrationThereafter, the reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b05a587565134ccfa6c4bd9182cbbbcf
Source dataset
uspto-grants-2013_02
Patent number
US08367724B2

Reaction notes

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