Triethylamine → HCID 15504838, compound

HRID 430875Notes

Reaction equation

HRID 430875 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[P:26]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=O)(=[O:4])=[O:3].C(N(CC)CC)C.Cl[SiH](Cl)Cl>C1(C)C(C)=CC=CC=1>[CH3:1][S:2]([NH:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[P:26]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24811TrichlorosilaneHCID 12010732HCID 12010732, compound2×

Product 1

HCID 15504838HCID 15504838, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
150 °C

Procedure

3.93 gram (7.17 mmol) of (−)-2-methylsulfonylamino-2′-diphenylphosphinyl-1,1′-binaphthyl (the formula (1-3a-1)) was dissolved in 179 ml of xylene in an autoclave, followed by the addition of 20.0 ml (143.4 mmol) of triethylamine at 0° C. over 15 minutes and 3.62 ml (35.8 mmol) of trichlorosilane over 30 minutes. The mixture was stirred at 150° C. for 18 hours in a tightly sealed condition. The reaction mixture was then extracted with 300 ml of ether. The extract was washed with 100 ml of saturated aqueous solution of ammonium chloride and 100 ml of brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure. The residue was purified using a silica gel column chromatography (eluent: 1:6 mixture of ethyl acetate and hexane) to obtain 3.35 gram of the titled compound.

Workup

  1. extractionThe reaction mixture was then extracted with 300 ml of ether
  2. washThe extract was washed with 100 ml of saturated aqueous solution of ammonium chloride and 100 ml of brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under a reduced pressure
  5. customThe residue was purified
  6. additiona silica gel column chromatography (eluent: 1:6 mixture of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-e6fbd90fce3944728d7b0a4f343eeeb2
Source dataset
uspto-grants-2001_11
Patent number
US06323353B1

Reaction notes

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