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Sodium Hydroxide → HCID 178436370, 화합물

HRID 2168575
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HRID 2168575 반응식
[BH-](OC(C)=O)(OC(C)=O)O[C:3](C)=O.[Na+].[CH:15]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][CH:18]=1)=[CH2:16].[C:25]1([P:31]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C-:32]2[CH:36]=[C:35]([C:37]([CH3:42])([CH2:39][CH:40]=O)[CH3:38])[CH:34]=[C:33]2[P:43]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(P(C(C)C)[C-]1C=CC=C1)(C)C.[Fe+2:74].[OH-].[Na+]>ClC(Cl)C>[C:25]1([P:31]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C-:32]2[CH:36]=[C:35]([C:37]([CH3:42])([CH2:39][CH2:40][CH2:3][NH:22][CH2:21][C:20]3[CH:23]=[CH:24][C:17]([CH:15]=[CH2:16])=[CH:18][CH:19]=3)[CH3:38])[CH:34]=[C:33]2[P:43]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH:50]([P:43]([CH:44]([CH3:49])[CH3:45])[C:33]1[C-:32]([P:31]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:36]=[CH:35][CH:34]=1)([CH3:55])[CH3:51].[Fe+2:74]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 110734664-Vinylbenzylamine (stabilized with MEHQ)HCID 178446967HCID 178446967, 화합물

생성물 1

HCID 178436370HCID 178436370, 화합물수율 62.3%

시약·촉매·용매 1

HCID 6365
1,1-Dichloroethane
용매
2회

실험 절차

A solution of NaBH(OAc)3 (0.17 g, 0.8 mmol) and 4-vinylbenzylamine (0.26 g, 1.95 mmol) in 10 ml of dichloroethane is admixed dropwise at ambient temperature with a solution of 1,2-bis-(diphenylphosphino)-1′-diisopropylphosphino-4-(4-oxo-2-methylbut-2-yl)ferrocene (1.3 g, 1.2 mmol) in 5 ml of dichloroethane. The solution is held with stirring for 24 hours and then neutralized by addition of 1M aqueous sodium hydroxide solution. The aqueous phase is extracted with 2 times 30 ml of dichloromethane. The organic phases are combined, dried over MgSO4, and concentrated under reduced pressure. The crude product obtained is purified by chromatography on silica gel (CH2Cl2/MeOH, 95:5) to give 0.4 g (ρ=55%) of 1,1′,2-tris(diphenylphosphino)-2′-diisopropylphosphino-4-[2-methyl-5-(4-vinylbenzylamino)pent-2-yl]ferrocene in the form of a red-orange powder. The 31P NMR spectrum preserves, as expected, the A2B spin system appearance typical of these triphosphines, as described by Hierso et al. for the nonheterogeneizable analog in Org. Lett. 2004, 6, 3473-3476, with slightly modified chemical shifts.

후처리

  1. extractionThe aqueous phase is extracted with 2 times 30 ml of dichloromethane
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product obtained
  5. customis purified by chromatography on silica gel (CH2Cl2/MeOH, 95:5)

출처 및 근거

ORD 기록
ord-8962ad32bddd43c0b87e181ab13bf4ca
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09045511B2

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