1,4-Dimethoxy-2-butyne → 2-(Trifluoroacetylamino)-5,6-bis(methoxymethyl)indane

HRID 2401581

反応式

HRID 2401581 の反応式
[CH3:1][O:2][CH2:3][C:4]#[C:5][CH2:6][O:7][CH3:8].[F:9][C:10]([F:22])([F:21])[C:11]([NH:13][CH:14]([CH2:18][C:19]#[CH:20])[CH2:15][C:16]#[CH:17])=[O:12]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh].C(O)C>[F:9][C:10]([F:21])([F:22])[C:11]([NH:13][CH:14]1[CH2:15][C:16]2[C:19](=[CH:20][C:5]([CH2:6][O:7][CH3:8])=[C:4]([CH2:3][O:2][CH3:1])[CH:17]=2)[CH2:18]1)=[O:12]

参加物

5

反応物 2

HCID 5423541,4-Dimethoxy-2-butyneHCID 224991802,2,2-trifluoro-N-[1-(2-propynyl)-3-butynyl]acetamide

生成物 1

HCID 224992202-(Trifluoroacetylamino)-5,6-bis(methoxymethyl)indane

試薬・触媒・溶媒 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)触媒HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

According to the procedure of Magnus et.al (Tetrahed. Lett., 34, 23-26 (1993)) a solution of commercially available 1,4-dimethoxy-2-butyne (1.32 g, 11.5 mmol) in nitrogen-degassed ethanol is heated to 80° C. with stirring under a nitrogen atmosphere. Tris(triphenylphosphine)rhodium chloride (64 mg, 0.07 mmol) and a solution of 2,2,2-trifluoro-N-[1-(2-propynyl)-3-butynyl]-acetamide (470 mg, 2.32 mmol; prepared from literature procedure: Romero, Arthur G.; Leiby, Jeffrey A PCT Int. Appl. WO 9623760) in nitrogen-degassed ethanol (2 ml) are added in portions over 2 hours. The mixture is stirred under nitrogen at 80° C. for a further 3 hours. The solvent is removed under vacuo and the residue is purified by flash chromatography on silica gel, eluting with hexane/ethyl acetate (2:1)

後処理

  1. customdegassed ethanol
  2. additionare added in portions over 2 hours
  3. stirringThe mixture is stirred under nitrogen at 80° C. for a further 3 hours
  4. customThe solvent is removed under vacuo
  5. customthe residue is purified by flash chromatography on silica gel
  6. washeluting with hexane/ethyl acetate (2:1)

出典と根拠

ORDレコード
ord-ea2f55b4c9a140e2a136f7b7bd8e6887
出典データセット
uspto-grants-2014_08
特許番号
US08796307B2

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