Triisopropylsilyl chloride → HCID 59523110, compound

HRID 1424773Notes

Reaction equation

[CH2:1]([O:13][C:14]1[N:15]=[CH:16][S:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Li]CCCC.[CH:24]([Si:27]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])Cl)([CH3:26])[CH3:25]>C1COCC1>[CH2:1]([O:13][C:14]1[N:15]=[C:16]([Si:27]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:24]([CH3:26])[CH3:25])[S:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 4.38 g (16.3 mmol) of 4-dodecyloxythiazole (10) in 150 mL of THF was cooled to −78° C. The resulting suspension was treated dropwise with 6.50 mL (16.3 mmol) of n-BuLi (2.5 M in hexanes). The mixture was stirred for 2 hours then the dry ice bath was removed for several minutes to form a yellow solution. The mixture was cooled to −78° C. and treated with 3.76 g (19.5 mmol) of triisopropylchlorosilane. The dry ice bath was removed and the mixture was stirred at ambient temperature for 90 minutes. The mixture was concentrated in vacuo and separated by flash chromatography (silica gel, 5.5×33 cm, chloroform) to give 6.24 g (90% yield) of compound 11 as a pale yellow oil. 1H NMR (500 MHz) δ 6.24 (s, 1H), 4.10 (t, 2H, J=6.7 Hz), 1.83 (m, 2H), 1.49-1.23 (m, 21H), 1.13 (d, 18H), 0.90 (t, 3H, J=7.0).

Workup

customthe dry ice bath was removed for several minutes
customto form a yellow solution
customThe dry ice bath was removed
stirringthe mixture was stirred at ambient temperature for 90 minutes
concentrationThe mixture was concentrated in vacuo
customseparated by flash chromatography (silica gel, 5.5×33 cm, chloroform)

Sources & evidence

ORD record: ord-9c3e64068d8147449d0201c365863af1
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927971B2

Reaction notes

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