Tributylamine → HCID 21832787, compound

HRID 1740718Notes

Reaction equation

HRID 1740718 reaction equation
[C:1]1([C:7]([C:48]2[CH:53]=[CH:52][C:51]([N:54]([CH3:56])[CH3:55])=[CH:50][CH:49]=2)([PH2:46]=O)[C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][C:19]=2[C:28]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([C:31]2[CH:36]=[CH:35][C:34]([N:37]([CH3:39])[CH3:38])=[CH:33][CH:32]=2)[PH2:29]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CCCC)CCCC)CCC.C1([SiH](Cl)Cl)C=CC=CC=1.[OH-].[Na+]>>[C:1]1([C:7]([C:48]2[CH:49]=[CH:50][C:51]([N:54]([CH3:56])[CH3:55])=[CH:52][CH:53]=2)([PH2:46])[C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][C:19]=2[C:28]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)([C:31]2[CH:36]=[CH:35][C:34]([N:37]([CH3:39])[CH3:38])=[CH:33][CH:32]=2)[PH2:29])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 7622TributylamineHCID 14798Sodium HydroxideHCID 74207Dichloro(phenyl)silaneHCID 178482825HCID 178482825, compound

Product 1

HCID 21832787HCID 21832787, compoundYield 75%

Conditions

Temperature
145 °C

Procedure

19.87 g (25.8 mmol) of 2,2'-bis(phenyl-4-dimethylaminophenyl-phosphinylmethyl)-1,1'-binaphthyl and 15.5 ml (66 mmol) of tributylamine are initially charged in 80 ml of degassed, dry o-xylene in an argon atmosphere while stirring and 9.4 ml (65 mmol) of phenyldichlorosilane are added dropwise. The mixture is subsequently heated at 145° C. for 7 hours while stirring. The reaction mixture is cooled, admixed with 50 ml of degassed 32% strength sodium hydroxide solution and the phases are separated. The organic phase is concentrated and the solid formed is filtered off and recrystallized from acetonitrile. This gives 14.3 g of colorless crystals, corresponding to a yield of 75%.

Workup

  1. customof degassed
  2. stirringwhile stirring
  3. temperatureThe reaction mixture is cooled
  4. customthe phases are separated
  5. concentrationThe organic phase is concentrated
  6. customthe solid formed
  7. filtrationis filtered off
  8. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-dd723524ed9c45c583009eb1318673d3
Source dataset
uspto-grants-1999_10
Patent number
US05972825

Reaction notes

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