Choline, hydroxide → HCID 86662345, compound

HRID 922004Notes

Reaction equation

[CH3:1]/[C:2](/[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])=[CH:3]\[CH2:4][O:5][C:6](=[O:12])[CH2:7][CH2:8][C:9]([OH:11])=[O:10].[OH-].[OH:20][CH2:21][CH2:22][N+:23]([CH3:26])([CH3:25])[CH3:24]>CO>[CH3:1]/[C:2](/[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])=[CH:3]\[CH2:4][O:5][C:6](=[O:12])[CH2:7][CH2:8][C:9]([O-:11])=[O:10].[OH:20][CH2:21][CH2:22][N+:23]([CH3:26])([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 0 °C

Procedure

Hemisuccinate [5] (1.0173 g, 4 mmol) was dissolved in 10 ml of methanol and chilled to 0° C. Choline hydroxide in (1.13 ml, 40% sol. in methanol, 4 mmol) was added dropwise and the reaction mixture was stirred for 5 min at 0° C. The solvent was evaporated and remaining volatile material was removed under reduced pressure (0.01 mbar) to yield product [6] as yellow liquid in quantitative yield. The product was pure according to 1H NMR without further purification. 1H-NMR (300 MHz, d6-DMSO) δ(ppm)=5.28 (t, J=7.0 Hz, 1H), 5.07 (t, J=6.8 Hz, 1H), 4.49 (d, J=7.0 Hz, 2H), 3.85 (m, 2H), 3.44 (m, 2H), 3.13 (s, 9H), 2.36 (t, J=7.2 Hz, 2H), 2.10 (t, J=7.2 Hz, 2H), 2.03 (m, 4H, 1.65 (s, 6H), 1.57 (s, 3H). 13C-NMR (75 MHz, d6-DMSO) δ(ppm)=174.0, 173.6, 140.7, 131.1, 123.8, 119.0, 67.3, 60.2, 55.0, 53.1, 39.3, 32.8, 31.2, 25.8, 25.5, 17.6, 16.2. Tg−65° C., T5%onset 170° C.

Workup

customThe solvent was evaporated
customwas removed under reduced pressure (0.01 mbar)

Sources & evidence

ORD record: ord-a940d1723a0948b1879e0a3a70ea545c
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278134B2

Reaction notes

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