Dimethylformamide → 5-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-6-methoxy-indan-1-one

HRID 460341

반응식

HRID 460341 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C:7](=[O:13])[CH2:6][CH2:5]2.Cl[CH2:15][CH:16]1[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH3:21][C:18]1([CH3:22])[O:17][CH:16]([CH2:15][O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][C:10]=2[O:11][CH3:12])[C:7](=[O:13])[CH2:6][CH2:5]3)[CH2:20][O:19]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 203744-(Chloromethyl)-2,2-dimethyl-1,3-dioxolaneHCID 147633955-Hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-one

생성물 1

HCID 184456735-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-6-methoxy-indan-1-one

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
95 °C

실험 절차

A mixture of 5-Hydroxy-6-indan-1-one, Intermediate H, (0.50 g, 0.0028 mol), 4-chloromethyl-2,2-dimethyl-1,3-dioxolane (0.766 mL, 0.0056 mol), potassium carbonate (1.54 g, 0.011 mol) and DMF (20.0 mL) was stirred at 95° C. for 3 days. Water (150.0 mL) was added and the mixture was extracted with ethyl acetate (2×150 mL). The organic layer was washed with sat. NaHCO3, brine and dried over Na2SO4. The solvent was then removed in vacuo to yield 5-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-6-methoxy-indan-1-one (Intermediate I) as light brown solid. MS m/z 293 (M+H)+.

후처리

  1. extractionthe mixture was extracted with ethyl acetate (2×150 mL)
  2. washThe organic layer was washed with sat. NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was then removed in vacuo

출처 및 근거

ORD 기록
ord-a7473ebca2bf4b33bce2e1449d44670e
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196110B2

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