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Sodium Hydroxide → HCID 178436370、化合物

HRID 2168575
ノート
印刷プレビュー

反応式

HRID 2168575 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 110734664-Vinylbenzylamine (stabilized with MEHQ)HCID 178446967HCID 178446967、化合物

生成物 1

HCID 178436370HCID 178436370、化合物収率 62.3%

試薬・触媒・溶媒 1

HCID 6365
1,1-Dichloroethane
溶媒
2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8962ad32bddd43c0b87e181ab13bf4ca
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…

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