Chloroform → 3,3-Diethoxy-1-propene

HRID 722749Notes

Reaction equation

[CH2:1]1CCCC[CH2:2]1.[C:7]([O:10][CH2:11][CH3:12])(=[O:9])[CH3:8].[CH:13](Cl)(Cl)Cl>>[CH3:12][CH2:11][O:10][CH:7]([O:9][CH2:1][CH3:2])[CH:8]=[CH2:13]

Participants

Reactant 2

HCID 6212Chloroform

HCID 21867204Cyclohexane ethylacetate

Product 1

HCID 624773,3-Diethoxy-1-propene

Procedure

Formula: C11H18O5 (MM=230.3) Rf: (cyclohexane/ethyl acetate: 85/15): 0.16 mp=35° C. {α}D20+23.18° (c 1.005, CHCl3) IR (film): 3089, 2977, 2933, 2871, 2822, 1464, 1441, 1424, 1382, 1323, 1282, 1262, 1232, 1168, 1144, 1107, 1045, 1028, 1002, 942, 912 cm−1 MS (m/z): 55 (83), 71 (100), 85 (38), 101 (31) 1H-NMR (500 MHz, CDCl3) 3.22 (2H, m), 3.31 (3H, m), 3.49 (3H, s), 3.50 (1H, t, J=10.2 Hz), 3.63 (3H, s), 4.06 (1H, dd, J=11.1 Hz, J=4.9 Hz), 4.18 (1H, dd, J=4.9 Hz, J=10.4 Hz), 4.97 (1H, d, J=4.1 Hz), 5.32 (1H, d, J=10.8 Hz), 5.48 (1H, d, J=17.4 Hz), 5.86 (1H, ddd, J=4.1 Hz, J=10.8 Hz, J=17.4 Hz) 13C-NMR (500 MHz, CDCl3) 59.2 (CH3), 60.9 (CH3), 68.5 (CH2), 68.5 (CH2), 71.3 (CH), 79.6 (CH), 81.5 (CH), 83.8 (CH), 100.5 (CH), 119.0 (CH2), 133.7 (CH)

Sources & evidence

ORD record: ord-b27f3f2a2df946608d5d97d1697481dd
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138531B2

Reaction notes

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