Dimethylformamide → (R)-3-(4-Methoxybenzyloxy)tetradecanoyl chloride

HRID 1022291Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][O:8][C@H:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:10][C:11](O)=[O:12])=[CH:5][CH:4]=1.CN(C)C=O.C(Cl)(=O)C([Cl:35])=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][O:8][C@H:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:10][C:11]([Cl:35])=[O:12])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of acid 34 (500 mg, 1.37 mmol) in DCM (5 mL) was added dimethylformamide (DMF) (100 mg, 1.37 mmol), and the resulting mixture was cooled to −10° C. Oxalyl chloride (174 mg, 1.37 mmol) in DCM (5 mL) was added dropwise. The solution was allowed to warm to room temperature over 1 h. After TLC analysis showed no acid present, the mixture was concentrated in vacuo and used without further purification.

Workup

temperatureto warm to room temperature over 1 h
concentrationthe mixture was concentrated in vacuo
customused without further purification

Sources & evidence

ORD record: ord-3ee8dfad493e4c908f533ee1b0ebe52a
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722064B2

Reaction notes

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