(2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R)-trans-3-formyl-2,2-dimethylcyclopropanecarboxylate → Fairytale

HRID 1976309Notes

Reaction equation

HRID 1976309 reaction equation
[CH3:1][C:2](C)([O-])C.[K+].[CH:7]([C@@H:9]1[C@@H:11]([C:12]([O:14][CH2:15][C:16]2[C:21]([F:22])=[C:20]([F:23])[C:19]([CH3:24])=[C:18]([F:25])[C:17]=2[F:26])=[O:13])[C:10]1([CH3:28])[CH3:27])=O>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.O1CCCC1>[CH3:27][C:10]1([CH3:28])[C@H:9](/[CH:7]=[CH:1]\[CH3:2])[C@H:11]1[C:12]([O:14][CH2:15][C:16]1[C:21]([F:22])=[C:20]([F:23])[C:19]([CH3:24])=[C:18]([F:25])[C:17]=1[F:26])=[O:13]

Participants

5

Reactant 2

HCID 15451879(2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R)-trans-3-formyl-2,2-dimethylcyclopropanecarboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 23731026FairytaleYield 67%

Reagents, catalysts & solvents 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 1.1 g of ethyltriphenylphosphonium bromide and 30 ml of terahydrofuran was cooled by ice and 0.23 g of potassium tert-butoxide was added to the mixture under stirring. After 15 minutes, a tetrahydrofuran (5 ml) solution containing 0.32 g of (2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R)-trans-3-formyl-2,2-dimethylcyclopropanecarboxylate was added to the mixture. After 30 minutes, the reaction mixture was filtered with celite and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=20/1) to give 0.22 g of (2,3,5,6-tetrafluoro-4-methylphenyl)methyl(1R)-trans-2,2-dimethyl-3-((Z)-1-propenyl)cyclopropanecarboxylate

Workup

  1. additionwas added to the mixture
  2. additionwas added to the mixture
  3. waitAfter 30 minutes
  4. filtrationthe reaction mixture was filtered with celite
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-404ab1dd152a4a6fb640c8da731a71dc
Source dataset
uspto-grants-2001_05
Patent number
US06225495B1

Reaction notes

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