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Potassium Carbonate → 6-Cyclopentyl-6-[2-(5-ethyl-4-hydroxy-2-propoxy-phenyl)-ethyl]-dihydro-pyran-2,4-dione

HRID 1438192
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HRID 1438192 반응식
[CH:1]1([C:6]([OH:32])([CH2:17][CH2:18][C:19]2[CH:24]=[C:23]([CH2:25][CH3:26])[C:22]([OH:27])=[CH:21][C:20]=2[O:28][CH2:29][CH2:30][CH3:31])[CH2:7][C:8]2[O:13]C(C)(C)O[C:10](=[O:16])[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH:1]1([C:6]2([CH2:17][CH2:18][C:19]3[CH:24]=[C:23]([CH2:25][CH3:26])[C:22]([OH:27])=[CH:21][C:20]=3[O:28][CH2:29][CH2:30][CH3:31])[O:32][C:10](=[O:16])[CH2:9][C:8](=[O:13])[CH2:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1
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4

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HCID 11430Potassium CarbonateHCID 587640776-[2-Cyclopentyl-4-(5-ethyl-4-hydroxy-2-propoxy-phenyl)-2-hydroxy-butyl]-2,2-dimethyl-[1,3]dioxin-4-one

생성물 1

HCID 587641376-Cyclopentyl-6-[2-(5-ethyl-4-hydroxy-2-propoxy-phenyl)-ethyl]-dihydro-pyran-2,4-dione수율 72%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
45 °C

실험 절차

6-[2-Cyclopentyl-4-(5-ethyl-4-hydroxy-2-propoxy-phenyl)-2-hydroxy-butyl]-2,2-dimethyl-[1,3]dioxin-4-one (0.8 g, 1.8 mmol,) was dissolved in methanol (15 mL), treated with potassium carbonate (0.74 g, 5.4 mmol) and heated at 45° C. under N2 for 90 mins. The reaction mixture was partitioned between H2O and IPE. The aqueous layer was made acidic with 1N HCl and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated to give the product as a yellow foam (0.5 g, 72% yield). 1H NMR (400 MHz, CDCl3): δ 1.02 (t, J=7.3 Hz, 3H), 1.19 (t, J=7.6 Hz, 3H), 1.41-1.87 (br m, 11H), 1.95 (m, 1H), 2.32 (m, 1H), 2.49-2.80 (m, 6H), 3.41 (m, 2H), 3.85 (m, 2H), 4.62 (s, 1H), 6.33 (s, 1H), 6.80 (s, 1H).

후처리

  1. customThe reaction mixture was partitioned between H2O and IPE
  2. extractionextracted with EtOAc
  3. washThe organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-383342abfd6a4a3e9b4193a49cc96642
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07622605B2

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