Water → HCID 178445629、化合物

HRID 1608894ノート

反応式

HRID 1608894 の反応式
[CH2:1]([C:4]1[CH:9]=[C:8]([F:10])[C:7](I)=[C:6]([F:12])[CH:5]=1)[CH2:2][CH3:3].[CH2:13]([C@H:17]1[CH2:22][CH2:21][C@H:20]([C@H:23]2[CH2:28][CH2:27][C@H:26]([C:29]#[CH:30])[CH2:25][CH2:24]2)[CH2:19][CH2:18]1)[CH2:14][CH:15]=[CH2:16].C(N(CC)CC)C.O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I.CCOCC>[CH2:13]([C@H:17]1[CH2:22][CH2:21][C@H:20]([C@H:23]2[CH2:24][CH2:25][C@H:26]([C:29]#[C:30][C:7]3[C:8]([F:10])=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][C:6]=3[F:12])[CH2:27][CH2:28]2)[CH2:19][CH2:18]1)[CH2:14][CH:15]=[CH2:16]

参加物

8

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 18979647HCID 18979647、化合物HCID 178455758HCID 178455758、化合物

生成物 1

HCID 178445629HCID 178445629、化合物収率 70.1%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 3283Diethyl Ether溶媒

反応条件

温度
90 °C

実験手順

A mixture of 0.65 g of 1-propyl-3,5-difluoro-4-iodobenzene (prepared according to Example 1a), 0.56 g of trans-4-[trans-4-(3-butenyl)cyclohexyl]cyclohexylacetylene, 0.053 g of tetrakis(triphenylphosphine)palladium (0), 0.009 g of copper(I) iodide and 6 ml of triethylamine was heated to 90° C. for 17 hrs. The reaction mixture was cooled, partioned between water and ether, the organic phase was separated and the aqueous phase was extracted several times with ether. The combined organic phases were dried over magnesium sulphate, filtered and evaporated. chromatography of the residue on silica gel with hexane and two-fold crystallization, firstly from hexane and then from isopropanol, gave 640 mg of 1-{trans-4-[trans-4-(3-butenyl)cyclohexyl]cyclohexylethynyl}-2,6-difluoro-4-propylbenzene, m.p. (C/N) 48.5° C., cl.p. (N/I) 189.8° C.

後処理

  1. temperatureThe reaction mixture was cooled
  2. customthe organic phase was separated
  3. extractionthe aqueous phase was extracted several times with ether
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customchromatography of the residue on silica gel with hexane and two-fold crystallization

出典と根拠

ORDレコード
ord-ab07ef6c16fb4eca8dc0bbd7161b8344
出典データセット
uspto-grants-1995_03
特許番号
US05399292

反応ノート

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