[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([CH2:9][OH:10])[CH:6]=[C:5]([CH2:11][OH:12])[CH:4]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.CO>C(Cl)Cl.CC(C)=O>[CH:9]([C:7]1[CH:6]=[C:5]([CH:11]=[O:12])[CH:4]=[C:3]([CH:2]=[O:1])[CH:8]=1)=[O:10]1,3,5-Tris(hydroxymethyl)benzene 15 (927 mg, 5.12 mmol) was suspended in CH2Cl2 (25 mL) and solid PCC (5.94 g, 27.6 mmol) was added. After 30 minutes of stirring, the reaction was diluted with acetone (10 mL) and was allowed to stir for 3 hr at RT. TLC (10% MeOH, 90% CH2Cl2 Rf=0.50) was used to determine if the reaction was complete. After the reaction was complete, the precipitated chromium salts were filtered off and washed with CH2Cl2. The aqueous layer was extracted 3 times in CH2Cl2 and saturated Na2CO3. The organic layers were combined and dried over anhydrous Na2SO4, filtered, and concentrated. Flash column chromatography (100% CH2Cl2 Rf=0.4) gave 16 (272 mg, 1.68 mmol, 33%). 1H NMR (CDCl3): δ 10.21 (s, 3H), 8.63 (s, 3H).
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