Reaction #5152

Reaction equation

1,5-Pentanediol

trimethylsilyl chloride

→

colorless oil

(CH3)3SiO(CH2)5OSi(CH3)3

Solvents

HMDS

HMDS

HMDS

Conditions

Workup

1. 1
   Otheran exothermic reaction
2. 2
   TemperatureHeating
3. 3
   Otherwas continued at 100° C.
4. 4
   Other(1 h), and 150° C. (2.5 h)
5. 5
   workup.DISTILLATIONDistillation

Procedure

1,5-Pentanediol (65 g, 0.62 mol) was placed in a 500 mL 3-necked RB flask and treated with 0.4 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 (130 mL, 0.71 mol 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. (1 h), and 150° C. (2.5 h). GC analysis (method 1) revealed excess HMDS and one product. Distillation provided 139 g of colorless oil, bp 47°-49° C./0.1 mm. 1H NMR (CDCl3): 3.60 (t, J=7Hz, 4H), 1.57 (m, 4H), 1.40 (m, 2H), 0.12 (s, 18H), consistent with the assigned structure.

Source