A challenge for Chemists and OOXML

Not all that long ago there were a series of competitions (of the new BBC version in that you could win kudos and little else) on various blogs (PMR, chemspiderman) to identify the number of chemicals in a paragraph of text. These focused largely on the difficultly of deciding what is and what is not a chemical – and consequently there was not necessarily a right answer.

Now I would like to propose a new challenge… and there is a right answer this time. I have randomly selected a preparation from an organic chemistry article a version of which is shown below. There is also a DOCX version available for download, which is fully and correctly formatted – to get the right answer I strongly suggest that you use the DOCX (although the latest version of Microsoft Office Word is not required).

So now for the challenge: how many chemicals do I think there are in the preparation – and for a further bonus point, which chemical did I get wrong?

((4S,5S)-5-Ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl)methanol (14)

To a stirring mixture of 13 (10.0 g, 62.5 mmol) and anhydrous K2CO3 (11.37 g, 81.25 mmol) in dry MeOH (240 mL) at 65 °C was added a solution of Bestmann–Ohira reagent (15.6 g, 81.25 mmol) in dry MeOH (80 mL) dropwise over a period of 6 h under an argon atmosphere. After neutralization with acetic acid, the solvent was removed in vacuo, water was added and the mixture extracted with ethyl acetate (2 × 100 mL). The combined organic extracts were dried over anhydrous Na2SO4, concentrated under reduced pressure and purified by column chromatography (pet. ether–ethyl acetate, 4 : 1) to obtain 14 (6.82 g, 70%) as a colorless liquid. [α]27D -8.6 (c 1.0, MeOH); anal. calcd for C8H12O3: C, 61.52; H, 7.74; found: C, 61.79; H, 7.84; IR (neat) ν max/cm-1, 3452, 3284, 2121, 848, 665; 1H NMR (200 MHz, CDCl3, D2O exchange), δ 1.42 (s, 3H), 1.48 (s, 3H), 2.53 (d, 1H, J = 2.15 Hz), 3.64 (dd, 1H, J = 12.25, 3.67 Hz), 3.87 (dd, 1H, J = 12.25, 3.03 Hz), 4.16 (ddd, 1H, J = 7.58, 3.67, 3.03 Hz), 4.56 (dd, 1H, J = 7.57, 2.15 Hz).


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