Triacetoxyperiodinane → HCID 71257714, compound

HRID 2200793Notes

Reaction equation

[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][C:12]3[N:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[N:15]=[C:14]([CH:22]([OH:24])[CH3:23])[CH:13]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:4]1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][C:12]3[N:17]=[C:16]([C:18]([F:20])([F:21])[F:19])[N:15]=[C:14]([C:22](=[O:24])[CH3:23])[CH:13]=3)[CH2:7][CH2:6]2)[O:1][CH2:2][CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

1-[6-(1,4-Dioxaspiro[4.5]dec-8-yloxy)-2-(trifluoromethyl)pyrimidin-4-yl]ethanol (0.20 g, 0.57 mmol) was dissolved in methylene chloride (5.00 mL) and cooled to 0° C. To this mixture, Dess-Martin periodinane (0.292 g, 0.689 mmol) was added. The mixture was stirred at 0° C. for 2 hours and then allowed to warm to 25° C. LCMS analysis indicated the reaction was complete. The mixture was extracted with EtOAc and the EtOAc extract was then washed with NaHCO3, sat. NaCl, dried and then the solvent was removed in vacuo to give the product, which was used in the next reaction. MS: 369 (M+Na+). 1H NMR (500 MHz, CDCl3): δ 7.35 (s, 1H); 5.33 (m, 1H, OCH); 3.95 (s, 411, OCH2); 2.63 (s, 3H, CH3); 1.99 (m, 4H); 1.82 (m, 2H); 1.63 (m, 2H). 13C NMR (125 MHz, CDCl3): δ 198 (s, O═C); 171 (s, OC); 161 (s, NC); 157 (q, N2C); 119 (q, CF3); 108 (s, CH and O2C); 74 (s, OCH); 65 (s, OCH2); 32 (s, CH2); 28 (s, CH2); 26 (s, CH3).

Workup

temperatureto warm to 25° C
extractionThe mixture was extracted with EtOAc
extractionthe EtOAc extract
washwas then washed with NaHCO3, sat. NaCl
customdried
customthe solvent was removed in vacuo
customto give the product, which
customwas used in the next reaction

Sources & evidence

ORD record: ord-1bc65022b97a4f58b9ebec9b1d0bccef
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359358B2

Reaction notes

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