Ammonium Chloride → Triisopropyl{[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thien-2-yl]methoxy}silane

HRID 9673

Reaction equation

[CH:1]([Si:4]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[O:5][CH2:6][C:7]1[S:8][CH:9]=[CH:10][C:11]=1[CH3:12])([CH3:3])[CH3:2].C([Li])CCC.C(O[B:28]1[O:32][C:31]([CH3:34])([CH3:33])[C:30]([CH3:36])([CH3:35])[O:29]1)(C)C.[Cl-].[NH4+]>O1CCCC1>[CH:16]([Si:4]([CH:1]([CH3:3])[CH3:2])([CH:13]([CH3:15])[CH3:14])[O:5][CH2:6][C:7]1[S:8][C:9]([B:28]2[O:32][C:31]([CH3:34])([CH3:33])[C:30]([CH3:36])([CH3:35])[O:29]2)=[CH:10][C:11]=1[CH3:12])([CH3:18])[CH3:17]

Participants

Conditions

Temperature: -78 °C

Procedure

A mixture of triisopropyl[(3-methylthien-2-yl)methoxy]silane (intermediate 115, 1.42 g) in tetrahydrofuran (20 ml), stirred at −78° C. under nitrogen, was treated with 1.6M butyllithium in hexanes (3.9 ml). The reaction temperature was slowly allowed to rise to 0° C. over 2 hours and then re-cooled to −78° C. 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.28 ml) was added and the reaction stirred at this temperature for 4 hours and then warmed to 0° C. The reaction was added to a mixture of saturated ammonium chloride and ice. The aqueous mixture was extracted with diethyl ether and the organic solution dried with brine and over sodium sulfate. Evaporation of the solvent afforded the title compound as a white solid

Workup

temperaturere-cooled to −78° C
stirringthe reaction stirred at this temperature for 4 hours
temperaturewarmed to 0° C
extractionThe aqueous mixture was extracted with diethyl ether
dry with materialthe organic solution dried with brine and over sodium sulfate
customEvaporation of the solvent

Sources & evidence

ORD record: ord-cc8ff98036344a30b32617317c2cefd3
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091237B2

Linked notes

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