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Triethylamine → Diethylaminoethyl ethyl 3-trifluoromethylbenzylphosphonate

HRID 1733814
ノート
印刷プレビュー

反応式

HRID 1733814 の反応式
[CH2:1]([O:3][P:4]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)(=[O:6])[OH:5])[CH3:2].C(Cl)(=O)C(Cl)=O.[CH2:24]([N:26]([CH:29](O)[CH3:30])[CH2:27][CH3:28])[CH3:25].C(N(CC)CC)C>C(Cl)Cl.O.CN(C=O)C>[F:16][C:14]([F:15])([F:17])[C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[CH2:7][P:4](=[O:5])([O:3][CH2:1][CH3:2])[O:6][CH2:25][CH2:24][N:26]([CH2:29][CH3:30])[CH2:27][CH3:28]
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

8

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 15819194Ethyl 3-trifluoromethylbenzylphosphonic acidHCID 158948401-(Diethylamino)ethanol

生成物 1

HCID 15819197Diethylaminoethyl ethyl 3-trifluoromethylbenzylphosphonate収率 10.7%

試薬・触媒・溶媒 3

HCID 962
Water
溶媒
HCID 6228Dimethylformamide溶媒
HCID 6344Dichloromethane溶媒3 回

反応条件

温度
0 °C

実験手順

Ethyl 3-trifluoromethylbenzylphosphonic acid, (7.55 g, 28 mmol) was dissolved in 100 mL of CH2Cl2 and cooled to 0° C. under nitrogen. After the oxalyl chloride (28 mmol) had been added, 0.5 mL of DMF was slowly added in 3 portions, and the resultant mixture was stirred at room temperature for 3 hours. Evaporation in vacuo gave the crude acid chloride which was dissolved in 90 mL of CH2Cl2 and added dropwise to a mixture of N,N-diethylaminoethanol (3.29 g, 28 mmol) and triethylamine (3.42 g, 34 mmol) in 60 mL of CH2Cl2 cooled at 0° C. The resultant mixture was allowed to warm to room temperature and stirred for 4 hours. Water was added (100 mL) and the aqueous phase was extracted 3 times with CH2Cl2. The combined organic extracts were dried with anhydrous Na2SO4, and evaporated to give the crude product as an oil. Purification was accomplished through column chromatography on silica gel using CH2Cl2 containing 2% MeOH and 0.1% NH3 and gave 1.1 g of the analytical product as an orange oil. D.C.I.M.S.[MH+, 368].

後処理

  1. customEvaporation in vacuo
  2. customgave the crude acid chloride which
  3. temperaturecooled at 0° C
  4. temperatureto warm to room temperature
  5. extractionthe aqueous phase was extracted 3 times with CH2Cl2
  6. dry with materialThe combined organic extracts were dried with anhydrous Na2SO4
  7. customevaporated
  8. customto give the crude product as an oil
  9. customPurification

出典と根拠

ORDレコード
ord-6159c71b85cf43409dcf824493b6fcba
出典データセット
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05532226

反応ノート

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