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

HRID 37430

反応式

HRID 37430 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
20 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-42837d0913d74dd8bbe8aa52a66453a6
出典データセット
uspto-grants-1995_05
特許番号
US05420273

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