Methyl acetoacetate → 5,6-Dihydro-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

HRID 357821

반응식

HRID 357821 반응식
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=O.[H-].[Na+].C([Li])CCC.[C:16]1([CH2:22][CH2:23][C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:25])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCCCCC.O1CCCC1>[C:26]1([C:24]2([CH2:23][CH2:22][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[O:25][C:1](=[O:6])[CH:2]=[CH:3][CH2:5]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

7

반응물 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 64802DihydrochalconeHCID 178418339Butyllithium

생성물 1

HCID 212224185,6-Dihydro-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

The title compound was prepared as described in General Method 1 using 25 mmol of methyl acetoacetate, 27.5 mmol of NaH 60% dispersion in oil, 26.25 mmol of 1.6M n-butyl lithium in hexane, 25 mmol of 3-phenylpropiophenone and 70 mL of tetrahydrofuran. Upon concentrating the reaction a solid precipitated out which was triturated with ether and filtered (m.p. 130°-130.55,° C.). 1H NMR (CDCl3) δ 2.2-2.4 (m, 2 H), 2.4-2.6 (m, 1 H), 2.6-2.8 (m, 1 H), 2.9 (d, 1 H), 3.0 (d, 1 H), 3.3 (d, 1 H), 3.4 (d, 1 H), 7.0-7.5 (m, 15 H).

후처리

  1. concentrationUpon concentrating
  2. customthe reaction a solid
  3. customprecipitated out which
  4. customwas triturated with ether
  5. filtrationfiltered (m.p. 130°-130.55,° C.)

출처 및 근거

ORD 기록
ord-775cf00caf8847c0a60c4dc573089d9b
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840751

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