Thiophenol → HCID 178516060, compound

HRID 2307180Notes

Reaction equation

[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].[Cs+].CS(O[C@H:15]1[CH2:20][CH2:19][C@@H:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][Si](C(C)(C)C)(C)C)=[CH:23][C:22]=2[O:35][Si](C(C)(C)C)(C)C)[CH2:17][CH2:16]1)(=O)=O.C(=O)([O-])O.[Na+]>CN(C)C=O>[C:1]1([S:7][C@H:15]2[CH2:16][CH2:17][C@H:18]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=3[OH:35])[CH2:19][CH2:20]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A round bottom flask containing thiophenol (30 μl, 0.29 mmol), cesium fluoride (44 mg, 0.29 mmol) and N,N-dimethylformamide (3 ml) was warmed at 40° C. for 1 hr. To this was added cis-4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl methanesulfonate (100 mg, 0.19 mmol) in N,N-dimethylformamide (1 ml) and the reaction mixture stirred at 50° C. for 18 hr. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate (10 ml) and extracted with ethyl acetate (3×20 ml). The combined organic extracts were washed with brine (10 ml), dried over magnesium sulfate and concentrated in vacuo. Purification via flash column chromatography (SiO2, ethyl acetate/petrol, 1:3) afforded the title compound (23 mg, 40%) as an off-white solid. δH (d4-MeOH) 1.40-1.57 (4H, m), 1.82-1.90 (2H, m), 2.04-2.16 (2H, m), 2.80 (1H, m), 3.13 (1H, m), 6.19-6.28 (2H, m), 6.88 (1H, d), 7.23 (1H, m), 7.30 (2H, m), 7.40 (2H, m); m/z (ES+) 301 (M+H)+.

Workup

extractionextracted with ethyl acetate (3×20 ml)
washThe combined organic extracts were washed with brine (10 ml)
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customPurification via flash column chromatography (SiO2, ethyl acetate/petrol, 1:3)

Sources & evidence

ORD record: ord-1e90b06602124e8ea80a652b44af7968
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06828460B2

Reaction notes

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