2-(2,5-Hexadiynyloxy)tetrahydro-2H-pyran → Pentadeca-2,5,8-triyn-1-ol tetrahydropyranyl ether

HRID 652113ノート

反応式

HRID 652113 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]#[C:10][CH2:11][C:12]#[CH:13].C([Mg]Br)C.Br[CH2:19][C:20]#[C:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>O1CCCC1.CCOCC.[Cl-].[NH4+]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]#[C:10][CH2:11][C:12]#[C:13][CH2:19][C:20]#[C:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

参加物

7

反応物 3

HCID 5340252-(2,5-Hexadiynyloxy)tetrahydro-2H-pyranHCID 109325492-Nonyne, 1-bromo-HCID 178418443HCID 178418443、化合物

生成物 1

HCID 13885163Pentadeca-2,5,8-triyn-1-ol tetrahydropyranyl ether

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 25517Ammonium Chloride溶媒

実験手順

To a stirred solution of 10.8 g (60 mmole) of hexa-2,5-diyn-1-ol tetrahydropyranyl ether [D. Van der Steen et al, Recueil 82, 1015 (1963)] in 100 ml of dry tetrahydrofuran there were added dropwise, under argon atmosphere, at 0°-5° C. 16.9 ml (0.60 mmol) of a 3.5N ethylmagnesium bromide solution in ether, maintaining the temperature at 0°-5° C. The mixture was stirred for 2 hours at 10°-15° C. and then 0.1 g of cuprous chloride were added. After 15 minutes a solution of 5.35 g (26 mmole) of 1-bromo-2-nonyne in 60 ml of dry tetrahydrofuran was added dropwise and the mixture stirred at room temperature for 3 hours. The reaction mixture was diluted with 70 ml of saturated ammonium chloride solution and extracted with methylene chloride. The organic extracts were dried and evaporated, and the residue purified by column chromatography on 450 g of silica gel, using hexane-ethyl acetate (99:1) as eluant, to provide pentadeca-2,5,8-triyn-1-ol tetrahydropyranyl ether.

後処理

  1. stirringthe mixture stirred at room temperature for 3 hours
  2. extractionextracted with methylene chloride
  3. customThe organic extracts were dried
  4. customevaporated
  5. customthe residue purified by column chromatography on 450 g of silica gel

出典と根拠

ORDレコード
ord-756a67987daa4c8fa983d9a53b6d6548
出典データセット
uspto-grants-1987_06
特許番号
US04670465

反応ノート

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