HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Hydroxide → HCID 178436370, compound

HRID 2168575
Notes
Print preview

Reaction equation

HRID 2168575 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

HCID 178436370HCID 178436370, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-8962ad32bddd43c0b87e181ab13bf4ca
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09045511B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes