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

HRID 1381323ノート

反応式

HRID 1381323 の反応式
[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]

参加物

7

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 54402789HCID 54402789、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒

反応条件

温度
120 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-e1ff6688a55444cd8669a787494891d6
出典データセット
uspto-grants-1986_04
特許番号
US04585885

反応ノート

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