Water → HCID 86628703, compound

HRID 2422927Notes

Reaction equation

[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH2:2][OH:3].[C:8]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.C(N(CC)CC)C.O>C(OCC)C>[C:8]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=[CH:12][C:11]([S:14]([O:3][CH2:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of ethyl glycolate (374 μl, 3.957 mmol) and biphenyl-4-sulfonyl chloride (1 g, 3.957 mmol) in anhydrous diethyl ether (2 ml) at 0° C. was treated dropwise with triethylamine (1.1 ml, 7.914 mmol). The temperature was maintained at 0° C. with stirring for a further 2 h. After this time, water was added and the phases separated. The aqueous phase was extracted with fresh diethyl ether. The combined organic extracts were dried (MgSO4), filtered and the solvent removed in vacuo. The crude product was purified by column chromatography over silica gel (Rf=0.26, 25% ethyl acetate in hexane) affording 16 as a colourless oil (1.055 g, 83%). δH (400 MHz, CDCl3) 1.25 (3H, t, J=6.8 Hz, CH3), 4.20 (2H, q, J=6.8 Hz, CH2), 4.65 (2H, s, CH2), 7.44-7.51 (3H, m, ArH), 7.61 (2H, d, J=7.6 Hz, ArH), 7.76 (2H, d, J=8 Hz, ArH), 8.01 (2H, d, J=8 Hz, ArH); δc (100.6 MHz, CDCl3) 14.2, 62.2, 65.0, 127.6, 128.1, 128.9, 129.0, 129.4, 134.4, 139.2, 147.4, 166.2; MS (ES+) 338.1 (100%, [M+H2O]+).

Workup

customthe phases separated
extractionThe aqueous phase was extracted with fresh diethyl ether
dry with materialThe combined organic extracts were dried (MgSO4)
filtrationfiltered
customthe solvent removed in vacuo
customThe crude product was purified by column chromatography over silica gel (Rf=0.26, 25% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-290e5cb5b52945638df651d25fa11bbd
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960434B2

Reaction notes

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