Water → HCID 178445629, 화합물

HRID 1608894노트

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HRID 1608894 반응식
[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]

참가 물질

8

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 18979647HCID 18979647, 화합물HCID 178455758HCID 178455758, 화합물

생성물 1

HCID 178445629HCID 178445629, 화합물수율 70.1%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 3283Diethyl Ether용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ab07ef6c16fb4eca8dc0bbd7161b8344
출처 데이터셋
uspto-grants-1995_03
특허 번호
US05399292

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