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Hydrochloric Acid → HCID 178441218、化合物

HRID 2168573
ノート
印刷プレビュー

反応式

HRID 2168573 の反応式
C(C1C=CC(CN)=CC=1)=C.[C:11]1([P:17]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C-:18]2[CH:22]=[C:21]([C:23]([CH3:33])([CH2:25]C[CH:27]3OCCC[O:28]3)[CH3:24])[CH:20]=[C:19]2[P:34]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:53]([C:57]1[CH:58]=[C:59]([P:75]([C:82]2[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=2)[C:76]2[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=2)[C-:60]([P:62]([C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[CH:61]=1)([CH3:56])([CH3:55])[CH3:54].[Fe+2:88].Cl>C1COCC1>[C:63]1([P:62]([C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[C-:60]2[CH:61]=[C:57]([C:53]([CH3:56])([CH2:54][CH:27]=[O:28])[CH3:55])[CH:58]=[C:59]2[P:75]([C:76]2[CH:77]=[CH:78][CH:79]=[CH:80][CH:81]=2)[C:82]2[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=2)[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1.[C:23]([C:21]1[CH:20]=[C:19]([P:34]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C-:18]([P:17]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:22]=1)([CH3:33])([CH3:24])[CH3:25].[Fe+2:88]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 110734664-Vinylbenzylamine (stabilized with MEHQ)HCID 178441217HCID 178441217、化合物

生成物 1

HCID 178441218HCID 178441218、化合物収率 96.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

For the deprotection leading to the actual compound of formula (9), with E=(CH2)3 and GF=4-vinyl-benzylamine, a solution of 1,1′,2,2′-tetrakis(diphenyl-phosphino)-4-[4-(1,3-dioxan-2-yl)-2-methylbut-2-yl]-4′-tert-butylferrocene (0.1 g, 88 μmol) in 20 ml of THF is admixed with 5 ml of 2N hydrochloric acid solution. The solution is placed under microwave radiation (125 W) according to the following program: temperature rise 10° C./min to 120° C., then plateau at 120° C. for 10 min. After cooling, the reaction mixture is concentrated under vacuum, diluted with 20 ml of water, and extracted with 2 times 25 ml of CH2Cl2. The organic phase is dried over MgSO4 and concentrated under reduced pressure. The crude product obtained is purified by chromatography on silica gel (eluent AcOEt/heptane 1:4) to give 90 mg (ρ=90%) of 1,1′,2,2′-tetrakis(diphenylphosphino)-4-(4-oxo-2-methylbut-2-yl)-4′-tert-butylferrocene in the form of a red powder, for which the 31P NMR spectrum preserves, as expected, the ABCD spin system appearance, with slightly modified chemical shifts.

後処理

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture is concentrated under vacuum
  3. additiondiluted with 20 ml of water
  4. extractionextracted with 2 times 25 ml of CH2Cl2
  5. dry with materialThe organic phase is dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product obtained
  8. customis purified by chromatography on silica gel (eluent AcOEt/heptane 1:4)

出典と根拠

ORDレコード
ord-47dd5bbfecb946b5826194942e8002d6
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09045511B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート