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Methyl acetoacetate → 5-(3,6-dihydro-4-hydroxy-6-oxo-2-phenyl-2H-pyran-2-yl)pentanoic acid

HRID 481867
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HRID 481867 반응식
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+:10].C([Li])CCC.[Na+].[C:17]([CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O-:31])=[O:30])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCCCCC.O1CCCC1>[OH:4][C:3]1[CH2:5][C:17]([CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:24][C:1](=[O:6])[CH:2]=1.[Na+:10].[C:17]([CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O-:31])=[O:30])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydride2회HCID 698361915-Benzoylpentanoic acid sodium saltHCID 178418339Butyllithium

생성물 2

HCID 546766295-(3,6-dihydro-4-hydroxy-6-oxo-2-phenyl-2H-pyran-2-yl)pentanoic acidHCID 698361915-Benzoylpentanoic acid sodium salt

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매2회

실험 절차

The title compound was prepared as described in General Method 1 using 25 nmol of methyl acetoacetate, 27.5 mmol of NaH 60% dispersion in oil, 26.25 mmol of 1.6M n-butyl lithium in hexane in 50 mL of tetrahydrofuran and 25 mmol of 5-benzoylpentanoic acid sodium salt in 100 mL of tetrahydrofuran. 5-Benzoylpentanoic acid sodium salt was prepared by reacting the acid (25 mmol) with hexane washed NaH (27.5 mmol) in tetrahydrofuran at 0° C. for 25 minutes. The crude solid was recrystallized from ethyl acetate (m.p. 136°-140° C.). 1H NMR (DMSO-d6) δ0.8-1.0 (m, 1H), 1.1-1.3 (m, 1H), 1.3-1.5 (m, 2H), 1.8-2.0 (m, 2H), 2.1 (t, 2H), 2.9 (ABq, 2H), 4.85 (s, 1H), 7.2-7.4 (m, 5H), 11.4 (bs, 1H), 12.0 (bs, 1H).

후처리

  1. customThe crude solid was recrystallized from ethyl acetate (m.p. 136°-140° C.)

출처 및 근거

ORD 기록
ord-3d5e8e82bfd14d9cb7f19c7946fd831f
출처 데이터셋
uspto-grants-1998_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05789440

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