Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 57814828, compound

HRID 1254171Notes

Reaction equation

[Cl:1][C@H:2]1[C@H:6]([CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])[C@@H:5](/[CH:19]=[CH:20]/[C@@H:21]([OH:28])[CH2:22][CH2:23][CH2:24][C@H:25]([OH:27])[CH3:26])[C@H:4]([O:29]C2CCCCO2)[CH2:3]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO.CCOC(C)=O>[Cl:1][C@H:2]1[C@H:6]([CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])[C@@H:5](/[CH:19]=[CH:20]/[C@@H:21]([OH:28])[CH2:22][CH2:23][CH2:24][C@H:25]([OH:27])[CH3:26])[C@H:4]([OH:29])[CH2:3]1

Participants

Conditions

Temperature: 22 °C

Procedure

A 20 mL vial equipped with a magnetic stirbar was charged with 175 mg (0.34 mmol) of TAP-ether 8 dissolved in 5 mL of methanol. To this was then added 300 mg (1.20 mmol) of pyridinium p-toluenesulfonate and the mixture was stirred at 22° C. over 7.5 h. The reaction was sampled by TLC (Rf of product was 0.6 in EtOAc) and worked up by concentration in vacuo to remove methanol. The residual products were taken up in ethyl acetate and filtered through a 22 g plug of silica gel, eluting the polar product away from the salts with ethyl acetate (350 mL). Concentration of the filtrate yielded 125 mg of product triol 9 as an oil; 1H NMR (CDCl3): 1.18 (d, J=6.3 hz, 3H), 1.34-1.62 (m, 5H), 1.69 (m, 2H), 1.84-2.38 (m, 11H), 2.47 (br s, 1H), 3.53 (br s, 1H), 3.70 (br s, 1H), 3.79 (br m, 1H), 3.99 (m, 1H), 4.08 (m, 2H), 4.57 (m, 2H), 5.18-5.60 (m, 6H), 5.91 (m, 1H).

Workup

customA 20 mL vial equipped with a magnetic stirbar
concentrationworked up by concentration in vacuo
customto remove methanol
filtrationfiltered through a 22 g plug of silica gel
washeluting the polar product away from the salts with ethyl acetate (350 mL)

Sources & evidence

ORD record: ord-5338ad1b45b246dca473f2d0b67e2b10
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455547B2

Reaction notes

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