Chlorotrimethylsilane → 3,8-Dioxa-2,9-disiladecane, 2,2,9,9-tetramethyl-

HRID 2210282

Reaction equation

HRID 2210282 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].[CH3:7][Si:8](Cl)([CH3:10])[CH3:9]>C[Si](N[Si](C)(C)C)(C)C>[Si:8]([O:5][CH2:4][CH2:3][CH2:2][CH2:1][O:6][Si:8]([CH3:10])([CH3:9])[CH3:7])([CH3:10])([CH3:9])[CH3:7]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 80641,4-Butanediol

Product 1

HCID 1403213,8-Dioxa-2,9-disiladecane, 2,2,9,9-tetramethyl-

Reagents, catalysts & solvents 1

HCID 13838HexamethyldisilazaneSolvent3×

Conditions

Temperature
50 °C

Procedure

1,4-Butanediol (54 g, 0.60 mol) was placed in a 500 mL 3-necked RB flask and treated with 0.3 mL trimethylsilyl chloride. A portion of HMDS (ca. 20 mL) was added, and an exothermic reaction took place as the mixture became homogeneous. The remainder of the HMDS (120 mL, 0.66 tool total) was added at a controlled rate (ca. 3-5 mL/min), maintaining the reaction temperature at ca. 50° C. Heating was continued at 100° C. (3 h), and 150° C. (1.5 h) GC analysis (method 1) revealed excess HMDS and one product. Distillation provided 127.8 g of colorless oil, bp 97°-99° C./15 mm. 1H NMR (CDCl3): 3.75-3.50 (m, 4H), 1.75-1.50 (m, 4H), 0.16 (s, 18H).

Workup

  1. customan exothermic reaction
  2. temperatureHeating
  3. customwas continued at 100° C.
  4. custom(3 h), and 150° C. (1.5 h) GC analysis (method 1)
  5. distillationDistillation

Sources & evidence

ORD record
ord-cbdab4d5425b4503888ca51212da8afd
Source dataset
uspto-grants-1995_10
Patent number
US05457215

Linked notes

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