Toluene → 4-(5-(3-(dimethylamino)prop-1-en-1-yl)thiophen-2-yl)-3-(1-hydroxyethyl)-1H-isochromen-1-one

HRID 634370

反応式

HRID 634370 の反応式
[Br-].[CH3:2][N:3]([CH3:25])[CH2:4][CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(C)C=CC=CC=1.[OH:43][CH:44]([C:46]1[O:47][C:48](=[O:63])[C:49]2[C:54]([C:55]=1[C:56]1[S:60][C:59]([CH:61]=O)=[CH:58][CH:57]=1)=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH3:45].[NH4+].[Cl-]>O1CCOCC1.CCOC(C)=O>[CH3:2][N:3]([CH3:25])[CH2:4][CH:5]=[CH:61][C:59]1[S:60][C:56]([C:55]2[C:54]3[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=3)[C:48](=[O:63])[O:47][C:46]=2[CH:44]([OH:43])[CH3:45])=[CH:57][CH:58]=1

参加物

8

反応物 5

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 2724136(2-(Dimethylamino)ethyl)triphenylphosphonium bromideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 118131138HCID 118131138、化合物

生成物 1

HCID 1237356434-(5-(3-(dimethylamino)prop-1-en-1-yl)thiophen-2-yl)-3-(1-hydroxyethyl)-1H-isochromen-1-one収率 40,858.102%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒2 回

実験手順

In a 100 ml 3-necked round bottomed flask (2-(dimethylamino)ethyl)-triphenylphosphonium bromide (1569 mg, 3.79 mmol) was loaded and suspended under Argon in 15 ml of Dioxane. Potassium bis(trimethylsilyl)amide solution 0.5 M in toluene (6.0 ml, 3.03 mmol) was added drop wise and a yellow\orange color appeared. The mixture was further stirred for 20 min then 5-(3-(1-hydroxyethyl)-1-oxo-1H-isochromen-4-yl)thiophene-2-carbaldehyde (Intermediate B37, 455 mg, 1.515 mmol) dissolved in 5 ml of dioxane was added The mixture was further stirred at rt for 2 h then poured into 100 ml of NH4Cl sat. sol. and 200 ml of EtOAc. Phases were separated and the organic one was dried over sodium sulfate. Solvents were removed and the crude was purified by chromatography eluting with DCM\20% MeOH in DCM mixtures to leave 4-(5-(3-(dimethylamino)prop-1-en-1-yl)thiophen-2-yl)-3-(1-hydroxyethyl)-1H-isochromen-1-one (220 mg, 0,619 mmol, 40.9% yield) as a yellow oil.

後処理

  1. additionwas added The mixture
  2. stirringwas further stirred at rt for 2 h
  3. customPhases were separated
  4. dry with materialthe organic one was dried over sodium sulfate
  5. customSolvents were removed
  6. customthe crude was purified by chromatography
  7. washeluting with DCM\20% MeOH in DCM mixtures

出典と根拠

ORDレコード
ord-c0c148c6293e483e94d77d900dc22546
出典データセット
uspto-grants-2016_04
特許番号
US09321776B2

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