Ammonium Chloride → 7,10-Dioxadispiro[2.2.4~6~.2~3~]dodecane

HRID 1665946ノート

反応式

HRID 1665946 の反応式
[CH2:1]=[C:2]1[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4][CH2:3]1.[CH2:12]([Zn]CC)C.IC(I)C.[NH4+].[Cl-]>C1(C)C=CC=CC=1>[CH2:12]1[C:2]2([CH2:11][CH2:10][C:5]3([O:6][CH2:7][CH2:8][O:9]3)[CH2:4][CH2:3]2)[CH2:1]1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 68980DiiodoethaneHCID 109537438-Methylidene-1,4-dioxaspiro[4.5]decaneHCID 178418750HCID 178418750、化合物

生成物 1

HCID 573366227,10-Dioxadispiro[2.2.4~6~.2~3~]dodecane

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 8-methylene-1,4-dioxa-spiro[4.5]decane (6.0 g, 39 mmol, prepared according to a literature procedure (K. C. Nicolaou, R. L. Magolda, D. A. Claremon, J. Am. Chem. Soc. 102 (1980) 1404-1409)) in toluene (10 mL), a solution of diethyl zinc (100 mL, 1 M in hexane) is added at −40 to −20° C. The mixture is stirred for 10 min before diiodoethane (53.6 g, 200 mmol) is added dropwise over a period of 20 min. The reaction is warmed to rt and stirring is continued for 18 h. The reaction mixture is poured onto ice-cooled sat. aq. NH4Cl solution and extracted twice with diethyl ether. The combined organic extracts are washed with sat. aq. Na2S2O3 and water, dried over Na2SO4, filtered and the solvent of the filtrate is evaporated to give 7,10-dioxa-dispiro[2.2.4.2]dodecane (12.35 g) as a colourless liquid containing approx. 20% of toluene (product volatile).

後処理

  1. additionis added dropwise over a period of 20 min
  2. additionThe reaction mixture is poured onto ice-
  3. extractionextracted twice with diethyl ether
  4. washThe combined organic extracts are washed with sat. aq. Na2S2O3 and water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent of the filtrate is evaporated

出典と根拠

ORDレコード
ord-8f682e6ba8464e17a8a0afc0026f8cdd
出典データセット
uspto-grants-2011_10
特許番号
US08039644B2

反応ノート

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