Oxalyl chloride → 5-(2-Hexyldecyl)-2-thiophenecarbonyl chloride

HRID 628229Notes

Reaction equation

[CH2:1]([CH:7]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:8][C:9]1[S:13][C:12]([C:14](O)=[O:15])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(Cl)(=O)C([Cl:28])=O>C(Cl)Cl>[CH2:1]([CH:7]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:8][C:9]1[S:13][C:12]([C:14]([Cl:28])=[O:15])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: 0 °C

Procedure

5-(2-Hexyldecyl)-2-thiophenecarboxylic acid (1.00 g, 2.84 mmol., 1.00 equiv.) and CH2Cl2 (5 mL) were added to a 10 mL schlenk flask. The solution was cooled to 0° C. Oxalyl chloride (0.60 mL, 6.5 mmol, 2.3 equiv.) was then added. The ice/water bath was left in place and the solution was stirred for 64 hours while warming to room temperature. The reaction mixture was concentrated to a clear brown liquid (931 mg, 88% yield). 1H NMR (400 MHz, CDCl3) δ 7.84 (d, J=3.9 Hz, 1H), 6.87 (d, J=3.8 Hz, 1H), 2.81 (d, J=6.7, 2H), 1.68 (b, 1H), 1.34-1.19 (m, 24H), 0.93-0.85 (m, 6H).

Workup

temperaturewhile warming to room temperature

Sources & evidence

ORD record: ord-2aef2b0d03974a3f91b2de5a7668cc44
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09312492B2

Reaction notes

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