Diethyl Ether → HCID 67529218, compound

HRID 1444773Notes

Reaction equation

C[I:2].[CH3:3][C:4]1[C:12]([CH3:14])([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:15][C:16]([OH:18])=[O:17])[CH:10]=2)[N:5]=1.[CH2:19](OCC)C>S1(CCCC1)(=O)=O>[I-:2].[C:16]([CH2:15][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N+:5]([CH3:19])=[C:4]([CH3:3])[C:12]2([CH3:13])[CH3:14])([OH:18])=[O:17]

Participants

Conditions

Temperature: 48 °C

Procedure

Methyl iodide (3 ml, 48.19 mmol) was added to a solution of 2,3,3-trimethyl-3H-indol-5-yl-acetic acid (2.5 g, 11.52 mmol) in sulfolan (15 ml). The reaction was heated at 48° C. for 18 hours, then cooled to room temperature. The crude reaction mixture was added dropwise to an excess of diethyl ether and the precipitate was collected by filtration and dried in vacuo to obtain the product as a beige solid (3.27 g, 79% yield). 1H NMR (d6-DMSO): δH 7.85 (d, 1H), 7.70 (s, 1H), 7.50 (d, 1H), 3.95 (s, 3H), 3.75 (s, 2H), 2.75 (s, 3H), 1.50 (s, 6H). MALDI-TOF, m/z 232 (M+=232 for C14H18NO2).

Workup

temperaturecooled to room temperature
customThe crude reaction mixture
filtrationthe precipitate was collected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-d03fd6d80c834c9faaa7046db80bad81
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662973B2

Reaction notes

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