4-(2-Morpholinoethoxy)benzaldehyde → 4-[2-[p-[(E)-2-(2,2-dimethyl-1,3-benzodithiol-5-yl)propenyl]phenoxy]ethyl]morpholine

HRID 37430

반응식

HRID 37430 반응식
[Br-].[CH3:2][C:3]1([CH3:33])[S:7][C:6]2[CH:8]=[CH:9][C:10]([CH:12]([P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH3:13])=[CH:11][C:5]=2[S:4]1.C([Li])CCC.[O:39]1[CH2:44][CH2:43][N:42]([CH2:45][CH2:46][O:47][C:48]2[CH:55]=[CH:54][C:51]([CH:52]=O)=[CH:50][CH:49]=2)[CH2:41][CH2:40]1>O1CCCC1.CCCCCC>[CH3:33][C:3]1([CH3:2])[S:7][C:6]2[CH:8]=[CH:9][C:10](/[C:12](/[CH3:13])=[CH:52]/[C:51]3[CH:50]=[CH:49][C:48]([O:47][CH2:46][CH2:45][N:42]4[CH2:41][CH2:40][O:39][CH2:44][CH2:43]4)=[CH:55][CH:54]=3)=[CH:11][C:5]=2[S:4]1

참가 물질

6

반응물 3

HCID 37199024-(2-Morpholinoethoxy)benzaldehydeHCID 19935456[1-(2,2-Dimethyl-1,3-benzodithiol-5-yl)ethyl]triphenylphosphonium bromideHCID 178418339Butyllithium

생성물 1

HCID 867449624-[2-[p-[(E)-2-(2,2-dimethyl-1,3-benzodithiol-5-yl)propenyl]phenoxy]ethyl]morpholine수율 35.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
20 °C

실험 절차

6.6 g of [1-(2,2-dimethyl-1,3-benzodithiol-5-yl)ethyl]triphenylphosphonium bromide were dissolved in 40 ml of tetrahydrofuran and treated slowly at 0° C. with 9 ml of a 1.5 molar solution of n-butyllithium in hexane. After 40 minutes, 3.5 g of 4-(2-morpholinoethoxy)benzaldehyde in 10 ml of tetrahydrofuran were added dropwise to the dark red solution and the mixture was stirred at 20° C. for 16 hours. The mixture was then poured on to ice and extracted with ethyl acetate. The combined extracts were washed with water, dried and evaporated. After chromatography (silica gel, eluting agent ethyl acetate) and crystallization from ether/hexane, there were obtained 1.8 g of 4-[2-[p-[(E)-2-(2,2-dimethyl-1,3-benzodithiol-5-yl)propenyl]phenoxy]ethyl]morpholine in the form of colorless crystals, melting point 90°-91° C.

후처리

  1. additionThe mixture was then poured on to ice
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with water
  4. customdried
  5. customevaporated
  6. washAfter chromatography (silica gel, eluting agent ethyl acetate) and crystallization from ether/hexane

출처 및 근거

ORD 기록
ord-42837d0913d74dd8bbe8aa52a66453a6
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420273

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