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

HRID 1976309ノート

反応式

HRID 1976309 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 23731026Fairytale収率 67%

試薬・触媒・溶媒 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-404ab1dd152a4a6fb640c8da731a71dc
出典データセット
uspto-grants-2001_05
特許番号
US06225495B1

反応ノート

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