Reaction #1929037

Reaction equation

Bromoacetyl bromide

Pyridine

ethylcyclopropanol

→

title compound

Yield 84.0%

1-ethylcyclopentyl 2-bromoacetate

Yield 84.0%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   workup.STIRRINGthe solution stirred at 0° C. for 20 h
2. 2
   FiltrationThe pyridinium bromide was filtered off
3. 3
   Washwashed with dichloromethane (2×300 mL)
4. 4
   WashThe combined organic layers were washed with water (4×750 mL)
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherThe crude oil was purified via of silica gel flash column chromatography (neutralized with TEA, 1:0 to 99:1 heptane:ethyl acetate)
7. 7
   ConcentrationAfter concentration
8. 8
   Filtrationthe oil was filtered

Procedure

Pyridine (67.5 g, 0.854 mol) was added dropwise to a solution of ethylcyclopropanol (75.0 g, 675 mmol) in anhydrous dichloromethane (750 mL) under N2 at 0° C. and stirred for 5 minutes. Bromoacetyl bromide (172 g, 74.4 mL, 854 mmol) in dichloromethane (75 mL) was added dropwise and the solution stirred at 0° C. for 20 h. The pyridinium bromide was filtered off, washed with dichloromethane (2×300 mL) and the solid pyridinium bromide discarded. The combined organic layers were washed with water (4×750 mL), and concentrated in vacuo. The crude oil was purified via of silica gel flash column chromatography (neutralized with TEA, 1:0 to 99:1 heptane:ethyl acetate). After concentration, the oil was filtered to afford the title compound (130 g, 84%) as a light orange oil. NMR (500 MHz, (CD3)2SO) δ: 3.93 (s, 2H), 2.07-2.14 (m, 2H), 2.00 (q, J=7 Hz, 2H), 1.59-1.77 (m, 4H), 0.89 (t, J=7 Hz, 3H).

Source