Chlorotrimethylsilane → Trimethyl[[1-methyl-3-[2,6,6-trimethyl-3-(trimethylsiloxy)-1,3-cyclohexadien-1-yl]-1-vinylallyl]oxy]silane

HRID 1381323Notes

Reaction equation

HRID 1381323 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[C:4]([CH:10]=[CH:11][C:12]([CH3:16])([OH:15])[CH:13]=[CH2:14])=[C:3]1[CH3:17].C(N(CC)CC)C.[CH3:25][Si:26]([CH3:29])([CH3:28])Cl.C(=O)([O-])O.[Na+]>CN(C)C=O.CCCCCC>[CH3:25][Si:26]([CH3:29])([CH3:28])[O:15][C:12]([CH3:16])([CH:13]=[CH2:14])[CH:11]=[CH:10][C:4]1[C:5]([CH3:8])([CH3:9])[CH2:6][CH:7]=[C:2]([O:1][Si:26]([CH3:29])([CH3:28])[CH3:25])[C:3]=1[CH3:17]

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 54402789HCID 54402789, compound

Product 1

HCID 54394290Trimethyl[[1-methyl-3-[2,6,6-trimethyl-3-(trimethylsiloxy)-1,3-cyclohexadien-1-yl]-1-vinylallyl]oxy]silane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 23.1 g of 96.5% 1-(3-oxo-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-1,4-pentadien-3-ol in 85 ml of dimethylformamide in a four-necked flask equipped with a stirrer and reflux condenser was treated with 80 ml of triethylamine and 73 ml of trimethylchlorosilane. The mixture was heated to reflux (heating bath temperature 120° C.) for 2 hours while stirring and under a light argon stream. The mixture was subsequently cooled to about 0° C. with an ice-bath and treated while stirring with 400 ml of hexane and 200 ml of semi-saturated sodium hydrogen carbonate solution. The phases were separated and the aqueous phase was extracted with 200 ml of hexane. The combined organic phases were washed once with 100 ml of saturated sodium chloride solution, dried over sodium sulphate and concentrated at 40° C. in a rotary evaporator. Distillation of the resulting brown oil (39.5 g) at 102°-107° C./0.1 Torr gave 35.0 g of trimethyl[[1-methyl-3-[2,6,6-trimethyl-3-(trimethylsiloxy)-1,3-cyclohexadien-1-yl]-1-vinylallyl]oxy]silane as a pale yellowish oil; purity about 77%.

Workup

  1. temperaturereflux condenser
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. temperatureThe mixture was subsequently cooled to about 0° C. with an ice-bath
  5. additiontreated
  6. customThe phases were separated
  7. extractionthe aqueous phase was extracted with 200 ml of hexane
  8. washThe combined organic phases were washed once with 100 ml of saturated sodium chloride solution
  9. dry with materialdried over sodium sulphate
  10. concentrationconcentrated at 40° C. in a rotary evaporator
  11. distillationDistillation of the resulting brown oil (39.5 g) at 102°-107° C./0.1 Torr

Sources & evidence

ORD record
ord-e1ff6688a55444cd8669a787494891d6
Source dataset
uspto-grants-1986_04
Patent number
US04585885

Reaction notes

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