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

HRID 322620Notes

Reaction equation

[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]

Participants

Reactant 5

HCID 679Dimethyl Sulfoxide

HCID 8471Triethylamine

HCID 65578Oxalyl chloride

HCID 119546104-(1,3-Dioxolan-2-yl)-6-methoxyhexan-1-ol

HCID 220112592-(2-Methoxyethyl)-pent-4-en-1-ol

Product 1

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

Procedure

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).

Sources & evidence

ORD record: ord-c367429025704763a6436343674029d3
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211360B1

Reaction notes

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