Chlorotrimethylsilane → HCID 11255491, compound

HRID 2058295Notes

Reaction equation

HRID 2058295 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][CH:15]=1.[CH3:24][Si:25]([CH3:28])([CH3:27])Cl>O1CCCC1.CCCCCC>[CH3:24][Si:25]([CH3:28])([CH3:27])[O:22][C:21]([O:23][Si:25]([CH3:28])([CH3:27])[CH3:24])=[CH:20][C:17]1[CH:16]=[CH:15][C:14]([Cl:13])=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 15880(4-Chlorophenyl)acetic acidHCID 178418339Butyllithium

Product 1

HCID 11255491HCID 11255491, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A cooled (0°-5° C.) solution of 41.4 g (0.41 mol) of diisopropylamine in 300 ml of tetrahydrofuran was treated slowly with butyllithium in hexane (250 ml of a 1.6 M solution, 0.4 mol). A solution of 34.12 g (0.2 mol) of p-chlorophenylacetic acid in 200 ml of tetrahydrofuran was added dropwise and the reaction mixture was stirred 30 minutes at 0° C. Trimethylchlorosilane (100 g) was added and the mixture was allowed to warm to room temperature and was stirred for 1.5 hours. The contents of the flask were filtered under nitrogen and the filtrate was evaporated under reduced pressure. The residue was dissolved in 80 ml of diethyl ether; the solution was filtered and the filtrate was evaporated. The resultant residue was distilled in a Vigreux column, maintaining the pot temperature below 130° C. to prevent decomposition of the product. The product β,β-bis(trimethylsiloxy)p-chlorostyrene, 32.56 g (52% yield), was obtained as a colorless liquid, bp 110° C. (0.1 mm); 1H NMR (CDCl3) δ7.0-7.4 (m, 4H), δ4.52 (s, 1H); δ0.22 (s) and δ0.26 (s) together 18H. The moisture sensitive product was stored under nitrogen.

Workup

  1. temperatureto warm to room temperature
  2. stirringwas stirred for 1.5 hours
  3. filtrationThe contents of the flask were filtered under nitrogen
  4. customthe filtrate was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in 80 ml of diethyl ether
  6. filtrationthe solution was filtered
  7. customthe filtrate was evaporated
  8. distillationThe resultant residue was distilled in a Vigreux column
  9. temperaturemaintaining the pot temperature below 130° C.

Sources & evidence

ORD record
ord-25c221e8f329414f900d69f181dc0101
Source dataset
uspto-grants-1980_07
Patent number
US04215044

Reaction notes

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