Methyl acetoacetate → 5,6-Dihydro-4-hydroxy-6-(pentafluorophenyl)-2H-pyran-2-one

HRID 481847

反応式

HRID 481847 の反応式
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[F:16][C:17]1[C:22](C=O)=[C:21]([F:25])[C:20]([F:26])=[C:19]([F:27])[C:18]=1[F:28]>CCCCCC.O1CCCC1>[OH:4][C:3]1[CH2:5][CH:8]([C:22]2[C:21]([F:25])=[C:20]([F:26])[C:19]([F:27])=[C:18]([F:28])[C:17]=2[F:16])[O:7][C:1](=[O:6])[CH:2]=1

参加物

7

反応物 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 69558PentafluorobenzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 547216805,6-Dihydro-4-hydroxy-6-(pentafluorophenyl)-2H-pyran-2-one

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

The title compound was prepared as described in General Method 1 using 2.5 mL of methyl acetoacetate, 1.0 g of NaH 60% dispersion in oil, 12.5 mL of 2.0M n-butyl lithium in hexane, 3.4 mL of pentafluorobenzaldehyde and 75 mL of tetrahydrofuran. After addition of the aldehyde, the reaction was stirred for 10 minutes at 0° C. then allowed to warm to room temperature overnight. The crude product was triturated from diethyl ether to afford a solid (m.p. 176°-178° C.). 1H NMR (CDCl3) δ2.89 (dd, 1H), 3.15 (dd, 1H), 3.70 (dd, 2H), 6.02 (dd, 1H).

後処理

  1. temperatureto warm to room temperature overnight
  2. customThe crude product was triturated from diethyl ether

出典と根拠

ORDレコード
ord-50c699337819497ab83a256ee9d7db3e
出典データセット
uspto-grants-1998_08
特許番号
US05789440

関連ノート

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