Carbon Tetrachloride → Ethyl 3,3-bis(4-fluorophenyl)-2-(1-methyl-1H-tetrazol-5-yl)-2-propenoate

HRID 974494

反応式

HRID 974494 の反応式
C(Cl)(Cl)(Cl)Cl.O1CCCC1.[F:11][C:12]1[CH:26]=[CH:25][C:15]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=O)=[CH:14][CH:13]=1.[CH3:27][N:28]1[C:32]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[N:31][N:30]=[N:29]1>N1C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl.O>[F:11][C:12]1[CH:26]=[CH:25][C:15]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[C:33]([C:32]2[N:28]([CH3:27])[N:29]=[N:30][N:31]=2)[C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:14][CH:13]=1

参加物

8

反応物 4

HCID 5943Carbon TetrachlorideHCID 8028TetrahydrofuranHCID 95824,4'-DifluorobenzophenoneHCID 283414Ethyl(1-methyl-1h-tetrazol-5-yl)acetate

生成物 1

HCID 14539522Ethyl 3,3-bis(4-fluorophenyl)-2-(1-methyl-1H-tetrazol-5-yl)-2-propenoate

試薬・触媒・溶媒 3

HCID 24193Titanium Tetrachloride触媒HCID 962Water溶媒HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

A mixture of titanium tetrachloride (2 mL) and carbon tetrachloride (2 mL) was added to 15 mL of tetrahydrofuran at -78° C. under an argon atmosphere. The suspension was stirred at -78° C. for 30 minutes before 0.2 g of 4,4'-difluorobenzophenone was added. After stirring for an additional 30 minutes, a solution of 0.15 g of ethyl 1-methyl-5-tetrazolylacetate in 1 mL of dry pyridine was added dropwise. The dark brownish suspension was stirred at -78° C. for 15 minutes, then was allowed to warm to 0° C. forming a thick paste. The mixture was allowed to stand for 24 hours at ambient temperature before it was poured into water. The aqueous mixture was extracted with ethyl acetate to yield crude product. Analytical TLC eluted five times with 20% (v/v) ethyl acetate in hexanes showed the desired product at Rf =0.3. Purification by preparative chromatography on two 20×20 cm2 0.25 mm TLC plates eluted twice with 20% (v/v) ethyl acetate in hexanes to give the title compound which was identical to the compound of Example 3, Step A.

後処理

  1. additionwas added
  2. stirringThe dark brownish suspension was stirred at -78° C. for 15 minutes
  3. customforming a thick paste
  4. waitto stand for 24 hours at ambient temperature before it
  5. extractionThe aqueous mixture was extracted with ethyl acetate
  6. customto yield crude product
  7. washAnalytical TLC eluted five times with 20% (v/v) ethyl acetate in hexanes
  8. customPurification by preparative chromatography on two 20×20 cm2 0.25 mm TLC plates
  9. washeluted twice with 20% (v/v) ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-f2cd5faaf30d4f4c9c7ad64557cf6a73
出典データセット
uspto-grants-1991_11
特許番号
US05068346

関連ノート

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