ChemicalBook CAS DataBase List 1,9-Dihydroxy-3,7-dioxanonane, 2,2μ-(Trimethylenedioxy)diethanol

1,9-Dihydroxy-3,7-dioxanonane, 2,2μ-(Trimethylenedioxy)diethanol synthesis

10synthesis methods

Product Name:1,9-Dihydroxy-3,7-dioxanonane, 2,2μ-(Trimethylenedioxy)diethanol
CAS Number:67439-82-1
Molecular formula:C7H16O4
Molecular Weight:164.2

77319-28-9 Synthesis

Acetic acid, 2,2'-[1,3-propanediylbis(oxy)]bis-, diethyl ester (9CI)

77319-28-9
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1,9-Dihydroxy-3,7-dioxanonane, 2,2μ-(Trimethylenedioxy)diethanol

67439-82-1
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$88.40/250mg

Yield: 90%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 0 - 10; for 1 h;

Steps:

2 Step 2-2-[3-(2-Hydroxyethoxy)propoxy]ethanol
To a solution of ethyl 2-[3-(2-ethoxy-2-oxo-ethoxy)propoxy]acetate (20.0 g, 80.5 mmol) in THF (300 mL) was added LiAlH₄(6.24 g, 161 mmol, 98% purity) at 0° C. The mixture was then stirred at 10° C. for 1 hour. On completion, the mixture was quenched with water (10 mL) and NaOH aqueous solution (15%, 10 mL) at 0° C., and the reaction was filtered. The filtrate was dried over Na₂SO₄, filtered and concentrated in vacuo to give the title compound (12 g, 90% yield) as colourless oil. ¹H NMR (400 MHz, DMSO-d₆) δ 4.53 (t, J=5.2 Hz, 2H), 3.50-3.45 (m, 4H), 3.43 (t, J=6.4 Hz, 4H), 3.37 (t, J=5.2 Hz 4H), 1.75-1.68 (m, 2H)

References:

Kymera Therapeutics, Inc.;Mainolfi, Nello;Ji, Nan;Kluge, Arthur F.;Weiss, Matthew M.;Zhang, Yi US2019/192668, 2019, A1 Location in patent:Paragraph 3132; 3134