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Triphenylphosphine → 3-Methyl-5-[3-[4-(5-difluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]propyl]-1,2,4-thiadiazole

HRID 266078
ノート
印刷プレビュー

反応式

HRID 266078 の反応式
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[S:9][N:8]=[C:7]([CH3:10])[N:6]=1.[F:11][CH:12]([F:27])[C:13]1[O:17][N:16]=[C:15]([C:18]2[CH:23]=[C:22]([CH3:24])[C:21](O)=[C:20]([CH3:26])[CH:19]=2)[N:14]=1.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:10][C:7]1[N:6]=[C:5]([CH2:4][CH2:3][CH2:2][O:1][C:21]2[C:20]([CH3:26])=[CH:19][C:18]([C:15]3[N:14]=[C:13]([CH:12]([F:11])[F:27])[O:17][N:16]=3)=[CH:23][C:22]=2[CH3:24])[S:9][N:8]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 189678815-(3-Hydroxypropyl)-3-methyl-1,2,4-thiadiazoleHCID 1355842214-(5-Difluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenol

生成物 1

HCID 189678883-Methyl-5-[3-[4-(5-difluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]propyl]-1,2,4-thiadiazole収率 81%

試薬・触媒・溶媒

1
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
20 °C

実験手順

A mixture of 5-(3-hydroxypropyl)-3-methyl-1,2,4-thiadiazole (242 mg, 1.53 mmol), 4-(5-difluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenol described in allowed U.S. patent application Ser. No. 07/869,287, incorporated herein by reference (400 mg, 1.67 mmol), and DEAD (290 mg, 1.67 mmol) was dissolved in 16 mL of THF. To the above solution was added triphenylphosphine (438 mg, 1.67 mmol) at 0° C. and the mixture was allowed to warm to 20° C. overnight. The solvent was removed in vacuo, an aqueous sodium bicarbonate solution was added, and the mixture was extracted with methylene chloride (7×). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica column chromatography (10 cm column, ethyl acetate/hexane, from 1/6 to 1/4) followed by recrystallization from ethyl acetate/hexane to afford 471 mg (81%) of 3-methyl-5-[3-[4-(5-difluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]propyl]-1,2,4-thiadiazole, as a white crystalline solid, m.p. 62°-64° C. 3-Methyl-5-[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-1,2,4-thiadiazole (I,Thi=3-methyl-1,2,4-thiadiazol-5-yl, Y=1,3-propylene, R1 =R2 =methyl, R3 =5-methyl-1,2,4-oxadiazol-3-yl)

後処理

  1. customThe solvent was removed in vacuo
  2. additionan aqueous sodium bicarbonate solution was added
  3. extractionthe mixture was extracted with methylene chloride (7×)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica column chromatography (10 cm column, ethyl acetate/hexane, from 1/6 to 1/4)
  7. customfollowed by recrystallization from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-7c43a460746b425fa58d1babc8f5caf3
出典データセット
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05650419

反応ノート

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