Triethylamine → HCID 54265840, compound

HRID 356503Notes

Reaction equation

[S:1](Br)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].CCN(CC)CC.[C:19]([C:23]1[CH:28]=[C:27]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[C:26]([CH3:37])=[CH:25][C:24]=1[SH:38])([CH3:22])([CH3:21])[CH3:20]>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[C:19]([C:23]1[CH:28]=[C:27]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:31])[CH3:32])[C:26]([CH3:37])=[CH:25][C:24]=1[S:38][S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2])([CH3:22])([CH3:21])[CH3:20]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of tosyl bromide (1.82 g, 7.76 mmol), Et3N (1.08 mL, 7.76 mmol), and CCl4 (15 mL) was cooled to 0° C. and treated with a solution of 2-tert-butyl-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-benzenethiol (prepared in Example III; 1.94 mmol) in CCl4 (15 mL) via addition funnel over a period of 45 minutes. The mixture was then allowed to warm to room temperature where it was stirred for 4 days. The mixture was diluted with CH2Cl2 and quenched with saturated NH4Cl. The layers were separated, the organic layer dried (Na2SO4) and the solvent removed in vacuo. The residue was submitted to column chromatography (3:1 hexanes:CH2Cl2 to 1:1 hexanes:CH2 Cl2) to provide the title compound. 1H NMR (CDCl3) δ 0.0 (s, 6 H), 0.78 (s, 9 H), 0.97 (s, 9 H), 1.84 (s, 3 H), 2.18 (s, 3 H), 6.60 (s, 1 H), 6.94-7.02 (m, 4 H), 7.25 (s, 1 H).

Workup

temperatureto warm to room temperature where it
customquenched with saturated NH4Cl
customThe layers were separated
dry with materialthe organic layer dried (Na2SO4)
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-0fb7a989231c4b4c8e5b3be6e7fb1b7c
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05834506

Reaction notes

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