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

HRID 2240809노트

반응식

HRID 2240809 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-44fae0d21cec40659f89e3b5c05fa2d3
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723378B2

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