Dimethyl Sulfoxide → 4-(1,3-Dioxolan-2-yl)-6-methoxyhexanal

HRID 322620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 322620
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH:6]([CH2:11][CH2:12][O:13][CH3:14])[CH2:7][CH2:8][CH2:9][OH:10].C(Cl)(C(Cl)=O)=O.CS(C)=O.C(N(CC)CC)C.COCCC(CC=C)CO>>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH:6]([CH2:11][CH2:12][O:13][CH3:14])[CH2:7][CH2:8][CH:9]=[O:10]

Komponenten

6

Edukt 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 119546104-(1,3-Dioxolan-2-yl)-6-methoxyhexan-1-olHCID 220112592-(2-Methoxyethyl)-pent-4-en-1-ol

Produkt 1

HCID 114130154-(1,3-Dioxolan-2-yl)-6-methoxyhexanalAusbeute 81 %

Versuchsvorschrift

The alcohol 7 (6 g, 29.37 mmol), prepared according to Example 6, was oxidized using 2M (COCl)2 (18 mL, 36 mmol), dry DMSO (5.1 mL, 72 mmol) and triethyl amine (20.7 mL, 144 mmol) analogous to the oxidation of the alcohol 4, as described in example 4. Similar work up as for 5 gave the aldehyde 8 (4.8 g, 81%) as a colorless oil. IR (KBr) υmax 2939, 2880, 2735, 1719, 1451, 1391, 1111, 1038, 947 cm−1: 1HNMR (CDCl3) δ1.45-2.85 (m, 5 H), 2.54 (t, J=6.8 Hz, 2 H), 3.31 (s, 3 H), 3.43-3.46 (m, 2 H), 3.83-3.95 (m, 4 H), 2.54 (t, J=6.8 Hz, 2 H), 3.31 (s, 3 H), 3.43-3.46 (m, 2 H), 3.83-3.95 (M, 4 H), 4.77 (d, J=3.3 Hz, 1 H), 9.76 (t, J=1.5 Hz, 1 H); 13CNMR (CDCl3) δ21.51, 29.23, 37.99, 41.72, 58.42, 64.81, 64.88, 70.66, 106.26, 202.39: mass spectrum (EI), m/z (rel intensity) 210 (33), 202 (M+, 3), 201 (15), 157 (19), 144 (27), 143 (38), 141 (19), 127 (17), 126 (1), 111 (30), 109 (12), 100 (4), 99 (11), 73 (100), 59 (10), 57 (8), 55 (12), 54 (5).

Quellen und Nachweise

ORD-Eintrag
ord-c367429025704763a6436343674029d3
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211360B1

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