Triethylamine → HCID 10694978, compound

HRID 430874Notes

Reaction equation

HRID 430874 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[P:22]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=O.C(N(CC)CC)C.Cl[SiH](Cl)Cl>C1(C)C(C)=CC=CC=1>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[P:22]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24811TrichlorosilaneHCID 11465546HCID 11465546, compound2×

Product 1

HCID 10694978HCID 10694978, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
150 °C

Procedure

7.16 gram (15.2 mmol) of (−)-2-amino-2′-diphenylphosphinyl-1,1′-binaphthyl (the formula (1-1a-1) was dissolved in 381 ml of xylene in an autoclave, followed by the addition of 42.5 ml (305.0 mmol) of triethylamine at 0° C. over 20 minutes and 7.70 ml (76.3 mmol) of trichlorosilane over 1 hour. The mixture was stirred at 150° C. for 18 hours in a tightly sealed condition. The reaction mixture was then extracted with 500 ml of ether. The extract was washed with 200 ml of saturated aqueous solution of ammonium chloride and 200 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: 1:4 mixture of ethyl acetate and hexane) to obtain 5.60 gram of the titled compound.

Workup

  1. extractionThe reaction mixture was then extracted with 500 ml of ether
  2. washThe extract was washed with 200 ml of saturated aqueous solution of ammonium chloride and 200 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: 1:4 mixture of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-860ba255239b49adba7da33a0aad6e70
Source dataset
uspto-grants-2001_11
Patent number
US06323353B1

Reaction notes

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