Chlorotrimethylsilane → 1-(2-Dimethylaminoethoxy)-1-trimethylsiloxy-2-methyl-1-propene

HRID 327269

反応式

HRID 327269 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[C:13]([O:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])(=[O:17])[CH:14]([CH3:16])[CH3:15].Cl[Si:25]([CH3:28])([CH3:27])[CH3:26]>O1CCCC1.CCCCCC>[CH3:23][N:21]([CH3:22])[CH2:20][CH2:19][O:18][C:13]([O:17][Si:25]([CH3:28])([CH3:27])[CH3:26])=[C:14]([CH3:16])[CH3:15]

参加物

7

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 4129962-Dimethylaminoethyl isobutyrateHCID 178418339Butyllithium

生成物 1

HCID 197346981-(2-Dimethylaminoethoxy)-1-trimethylsiloxy-2-methyl-1-propene収率 62.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 31.78 g (44 mL, 0.314 mol) of diisopropylamine (Aldrich gold label) in 300 mL of tetrahydrofuran at -5° to 0° C. was added over a period of about 30 min. 0.314 mol of 1.6N n-butyl lithium in hexane (196 mL). After 30 min at 0° C., the solution was cooled to -78° C. and 50 g (0.314 mol) of 2-dimethylaminoethyl isobutyrate, prepared as above, was added keeping the temperature below -70° C. Then 34.11 g (39.9 mL, 0.314 mol) of chlorotrimethylsilane was added below -70° C. After warming to room temperature, the mixture was concentrated on a rotary evaporator, and the residue was treated with hexane and filtered under argon. The filtrate was concentrated on a rotary evaporator and distilled in a spinning band column to give 45.4 g of 1-(2-dimethylaminoethoxy)-1-trimethylsiloxy-2-methyl-1-propene, b.p. 39°-42.5° C. (0.5 mm). 1H-NMR (360 MHz, benzene-d6): 0.22 (s, 9 H, SiMe), 1.67 (s, 3 H, =CCH3), 1.77 (s, 3 H, =CCH3), 2.12 (s, 6 H, NCH3), 2.46 (t, J=6 Hz, 2 H, CH2N), 3.85 (t, J=6 Hz, 2 H, CH2O). Anal Calcd for C11H25O2SiN: C 57.09, H 10.89, N 6.05, Si 12.14. Found: C 57.27, H 11.11, N 6.17, Si 11.37. IR (neat): 1705 cm-1 (C=C), no C=O absorption.

後処理

  1. additionwas added
  2. customthe temperature below -70° C
  3. temperatureAfter warming to room temperature
  4. concentrationthe mixture was concentrated on a rotary evaporator
  5. additionthe residue was treated with hexane
  6. filtrationfiltered under argon
  7. concentrationThe filtrate was concentrated on a rotary evaporator
  8. distillationdistilled in a spinning band column

出典と根拠

ORDレコード
ord-323de6ff9fd74090ab335df6b9ef8100
出典データセット
uspto-grants-1993_12
特許番号
US05272201

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