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Methyl iodide → 6'-((3,3-Difluorocyclobutyl)methoxy)-4-methoxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-one

HRID 1468072
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HRID 1468072 반응식
[F:1][C:2]1([F:24])[CH2:5][CH:4]([CH2:6][O:7][C:8]2[CH:16]=[C:15]3[C:11]([CH2:12][C:13]4([CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]4)[C:14]3=[O:17])=[CH:10][CH:9]=2)[CH2:3]1.[CH3:25]C(C)([O-])C.[K+].CI.CCOC(C)=O>C1COCC1.CCCCCCC>[F:1][C:2]1([F:24])[CH2:5][CH:4]([CH2:6][O:7][C:8]2[CH:16]=[C:15]3[C:11]([CH2:12][C:13]4([CH2:22][CH2:21][CH:20]([O:23][CH3:25])[CH2:19][CH2:18]4)[C:14]3=[O:17])=[CH:10][CH:9]=2)[CH2:3]1
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참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 867067206'-((3,3-Difluorocyclobutyl)methoxy)-4-hydroxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-one2회

생성물 1

HCID 867067216'-((3,3-Difluorocyclobutyl)methoxy)-4-methoxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-one수율 59.7%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8900Heptane용매

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온도
0 °C

실험 절차

6′-((3,3-difluorocyclobutyl)methoxy)-4-hydroxyspiro[cyclohexane-1,2′-inden]-1′ (3′H)-one (Intermediate 13, 2.98 g, 8.85 mmol) was dissolved in THF (35 mL) under an atmosphere of nitrogen, and the solution was cooled to 0° C. Potassium tert-butoxide (2.98 g, 26.6 mmol) was added portionwise and the mixture was stirred at 0° C. for 15 min. Methyl iodide (1.11 mL, 17.7 mmol) was added. The cooling bath was removed, and the mixture was stirred at r.t. overnight. Water (200 mL) was added and the resulting solution was partitioned between additional water (200 mL) and EtOAc (400 mL). The organic phases was dried (MgSO4) and concentrated, and the product was isolated using column chromatography (0-50% EtOAc in heptane) providing 1.85 g (59% yield) of the title compound. MS (ES+) m/z 351 [M+H]+.

후처리

  1. customThe cooling bath was removed
  2. stirringthe mixture was stirred at r.t. overnight
  3. additionWater (200 mL) was added
  4. customthe resulting solution was partitioned between additional water (200 mL) and EtOAc (400 mL)
  5. dry with materialThe organic phases was dried (MgSO4)
  6. concentrationconcentrated
  7. customthe product was isolated

출처 및 근거

ORD 기록
ord-2872036075ba41ef9f87f3db67ef2b89
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09000185B2

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