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

HRID 481847

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HRID 481847 반응식
[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

참가 물질

7

반응물 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 69558PentafluorobenzaldehydeHCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

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온도
0 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-50c699337819497ab83a256ee9d7db3e
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05789440

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