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Hydrochloric Acid → HCID 178441218, 화합물

HRID 2168573
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HRID 2168573 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 110734664-Vinylbenzylamine (stabilized with MEHQ)HCID 178441217HCID 178441217, 화합물

생성물 1

HCID 178441218HCID 178441218, 화합물수율 96.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-47dd5bbfecb946b5826194942e8002d6
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09045511B2

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