p-(2-(Dimethylamino)ethoxy)benzaldehyde → 2-[p-[(E)-2-(3,4-dihydro-4,4-dimethyl-2H--benzothiopyran-6-yl)propenyl]phenoxy]-N,N-dimethylethylamine

HRID 37441

반응식

HRID 37441 반응식
[Br-].[CH3:2][C:3]1([CH3:34])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:13]([P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH3:14])[CH:11]=2)[S:6][CH2:5][CH2:4]1.C([Li])CCC.[CH3:40][N:41]([CH3:53])[CH2:42][CH2:43][O:44][C:45]1[CH:52]=[CH:51][C:48]([CH:49]=O)=[CH:47][CH:46]=1>O1CCCC1>[CH3:34][C:3]1([CH3:2])[C:12]2[CH:11]=[C:10](/[C:13](/[CH3:14])=[CH:49]/[C:48]3[CH:51]=[CH:52][C:45]([O:44][CH2:43][CH2:42][N:41]([CH3:40])[CH3:53])=[CH:46][CH:47]=3)[CH:9]=[CH:8][C:7]=2[S:6][CH2:5][CH2:4]1

참가 물질

5

반응물 3

HCID 84823p-(2-(Dimethylamino)ethoxy)benzaldehydeHCID 19935432[1-(4,4-Dimethyl-6-thiochromanyl)ethyl]triphenylphosphonium bromideHCID 178418339Butyllithium

생성물 1

HCID 677834662-[p-[(E)-2-(3,4-dihydro-4,4-dimethyl-2H--benzothiopyran-6-yl)propenyl]phenoxy]-N,N-dimethylethylamine수율 44.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

32 g of [1-(4,4-dimethyl-6-thiochromanyl)ethyl]triphenylphosphonium bromide were suspended in 130 ml of tetrahydrofuran and treated at 0° C. with 37 ml of n-butyllithium (1.6 molar in hexane). After stirring at 0° C. for 45 minutes, a solution of 10 g of 4-(2-dimethylaminoethoxy)benzaldehyde in 60 ml of tetrahydrofuran was added dropwise to the orange reaction mixture. The mixture was stirred at room temperature for an additional 1 hour, poured on to ice/water and extracted with ether. The organic phases were washed with water, dried and evaporated. After filtration of the crude product over neutral Alox (eluting agent ether) and recrystallization from hexane/ether, there were obtained 8.7 g of 2-[p-[(E)-2-(3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)propenyl]phenoxy]-N,N-dimethylethylamine, melting point 81°-82° C.

후처리

  1. stirringThe mixture was stirred at room temperature for an additional 1 hour
  2. extractionextracted with ether
  3. washThe organic phases were washed with water
  4. customdried
  5. customevaporated
  6. filtrationAfter filtration of the crude product
  7. washover neutral Alox (eluting agent ether) and recrystallization from hexane/ether

출처 및 근거

ORD 기록
ord-60610fa263774d419fa3d8889eeb31c1
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420273

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