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 373577

反応式

HRID 373577 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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 in 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--benzothiopyran-6-yl)propenyl]phenoxy]-N,N-dimethylethylamine, melting point 81°-82° C.

後処理

  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

出典と根拠

ORDレコード
ord-893fd564fd974012a4f599034524678c
出典データセット
uspto-grants-1992_11
特許番号
US05164387

関連ノート

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