1-cyclopropylcyclopropan-1-ol synthesis

5synthesis methods

Product Name:1-cyclopropylcyclopropan-1-ol
CAS Number:54251-80-8
Molecular formula:C6H10O
Molecular Weight:98.14

2868-37-3 Synthesis

2868-37-3
267 suppliers
$10.00/25g

925-90-6 Synthesis

925-90-6
343 suppliers
$12.00/5ml

54251-80-8
16 suppliers
$398.00/1g

Yield:54251-80-8 91%

Reaction Conditions:

with titanium isopropoxide in 2-methyltetrahydrofuran at 15 - 20; for 4 h;Solvent;Temperature;

Steps:

1.1; 41 Step 1: Synthesis of [1,1′-bi(cyclopropan)]-1-ol (18)

A solution of methyl cyclopropanecarboxylate (109 g, 1.09 mol) in 2-MeTHF (1.31 L) and titanium(IV) isopropoxide (71 mL, 240.6 mmol) was stirred in a Morton flask then cooled to 18° C. Ethylmagnesium bromide (753 mL of 3 M, 2.259 mol) was added dropwise over 2 h to control the temperature between 15 to 20° C. The mixture was stirred for another 2 h then cooled to 5° C. and quenched drop-wise (slowly) with cold (5-10° C.) NaHSO₄(1.31 L of 20% w/v, 2.182 mol) while keeping the temperature below 10° C. The organic phase was isolated and the aqueous phase was re-extracted with hexanes (500 mL). The aqueous phase was discarded. The organic phases were combined, washed with sat. aq. NaHCO₃(200 mL of 10% w/v, 238 mmol), dried over Na₂SO₄, and concentrated (30° C./40 torr) to afford 108.6 g of [1,1′-bi(cyclopropan)]-1-ol as a pale yellow liquid. The sample contained 8 wt % 2-MeTHF and 2 wt % iPrOH by ¹H NMR, so the corrected yield of the desired product was 91%.¹H NMR (400 MHz, Chloroform-d) δ 1.99 (s, 1H), 1.35 (tt, J=8.2, 5.1 Hz, 1H), 1.22 (dd, J=9.0, 6.1 Hz, 1H), 0.70-0.65 (m, 2H), 0.52-0.45 (m, 2H), 0.43-0.38 (m, 2H), 0.21-0.15 (m, 2H).

References:

US2021/47345,2021,A1 Location in patent:Paragraph 0418-0420; 0756; 0757