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

HRID 1468072
ノート
印刷プレビュー

反応式

HRID 1468072 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 867067206'-((3,3-Difluorocyclobutyl)methoxy)-4-hydroxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-one2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8900Heptane溶媒

反応条件

温度
0 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-2872036075ba41ef9f87f3db67ef2b89
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09000185B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート