Chlorotrimethylsilane → HCID 14371698, compound

HRID 2073603Notes

Reaction equation

HRID 2073603 reaction equation
[CH3:1][C:2]1([CH3:31])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6](/[C:14](/[CH3:30])=[CH:15]/[C:16]3[CH:21]=[CH:20][C:19]([P:22]([O:27]CC)(=[O:26])[O:23]CC)=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.[Br-].[Na+].C[Si](C)(C)Cl>C(#N)C>[CH3:1][C:2]1([CH3:31])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6](/[C:14](/[CH3:30])=[CH:15]/[C:16]3[CH:21]=[CH:20][C:19]([P:22]([OH:26])(=[O:23])[OH:27])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 253881Sodium BromideHCID 14371697HCID 14371697, compound

Product 1

HCID 14371698HCID 14371698, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2 g (4.5 millimoles) of diethyl (E)-4-[2(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1propenyl]-benzenephosphonate, 1.86 g (18 millimoles) of sodium bromide and 3 g (27 millimoles) of trimethylchlorosilane in 10 ml of acetonitrile were stirred for 3 hours at 40° C. The mixture was then allowed to cool and was filtered, and the filtrate was evaporated down. The oil which remained was stirred for 30 minutes with water at room temperature and then extracted with ether, and the organic phase was washed with water, dried over sodium sulfate and evaporated down. Recrystallization of the residue from ethyl acetate gave 1.1 g of the title compound of melting point 208°-209° C.

Workup

  1. temperatureto cool
  2. filtrationwas filtered
  3. customthe filtrate was evaporated down
  4. extractionextracted with ether
  5. washthe organic phase was washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated down
  8. customRecrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-ed09cfba7f9545a992065df2b142317f
Source dataset
uspto-grants-1990_04
Patent number
US04918212

Reaction notes

Loading…