Potassium Iodide → HCID 86731604, compound

HRID 1746441Notes

Reaction equation

[CH3:1][C:2]([CH3:26])([Si:4]([CH3:25])([CH3:24])[O:5][CH2:6][CH:7]([C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1)[CH2:8][O:9][Si:10]([CH3:16])([CH3:15])[C:11]([CH3:14])([CH3:13])[CH3:12])[CH3:3].[CH2:27](O)[CH:28]([CH3:30])[CH3:29].[I-].[K+]>O.ClCCl>[CH2:27]([NH:21][C:20]1[CH:22]=[CH:23][C:17]([CH:7]([CH2:8][O:9][Si:10]([CH3:15])([CH3:16])[C:11]([CH3:12])([CH3:13])[CH3:14])[CH2:6][O:5][Si:4]([CH3:24])([CH3:25])[C:2]([CH3:26])([CH3:1])[CH3:3])=[CH:18][CH:19]=1)[CH:28]([CH3:30])[CH3:29]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-(2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecan-6-yl)aniline (193.1 mg, 0.488 mmol), isobutanol (0.090 mL, 0.976 mmol), potassium iodide (162 mg, 0.976 mmol), [Cp*IrCl2]2 (3.89 mg, 4.88 μmol) and water (3 mL) was prepared in a microwave vial. The reaction vessel was sealed and heated by microwaves to 150° C. for 1.5 hours. After cooling, the solution was diluted with water and dichloromethane (20 mL), then the organic phase separated (hydrophobic frit) and concentrated in vacuo. The crude was purified by flash silica (Si) chromatography (using a 0-100% dichloromethane-cyclohexane gradient) to give the desired product, 155.9 mg. LCMS (M+1) 452, RT 1.96 mins.

Workup

customwas prepared in a microwave vial
customThe reaction vessel was sealed
temperatureAfter cooling
customthe organic phase separated (hydrophobic frit)
concentrationconcentrated in vacuo
customThe crude was purified by flash silica (Si) chromatography (

Sources & evidence

ORD record: ord-5ceb9ab088c4419b862c0106a0b88a3c
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150508B2

Reaction notes

Loading…