tert-Butanol → HCID 118481847, compound

HRID 626293Notes

Reaction equation

HRID 626293 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2C=CC3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[O:9]2)[CH:5]=[CH:6][CH:7]=1.C[N+]1([O-])CC[O:22]CC1.C[C:27]([OH:30])([CH3:29])[CH3:28]>C1COCC1.O.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:29]([OH:22])[C@@H:27]([OH:30])[C:28]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[O:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 75985386HCID 75985386, compound

Product 1

HCID 118481847HCID 118481847, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-chlorophenyl)-2H-chromene (2i) (72.8 mg, 0.3 mmol) and 4-methylmorpholine N-oxide (52.7 mg, 0.45 mmol) in THF (3 mL) and water (0.116 mL) was added a 2.5 wt % solution of osmium tetraoxide in t-BuOH (0.118 mL). The mixture was stirred at 23 C for 16 h and was then quenched with a saturated solution of sodium thiosulfate. The mixture was extracted with EtOAc. The combined organics was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude was purified by flash chromatography using 20% EtOAc/hexanes to afford 9 as an off-white solid (76 mg, 91%). Analytical data for 9: 1H NMR (500 MHz, CDCl3) δ 7.53-7.48 (m, 1H), 7.39 (dd, J=7.6, 1.7 Hz, 1H), 7.37 (d, J=1.4 Hz, 3H), 7.30 (ddd, J=8.6, 7.3, 1.7 Hz, 1H), 7.02 (td, J=7.4, 1.2 Hz, 1H), 6.96 (dd, J=8.2, 1.1 Hz, 1H), 5.05 (d, J=9.5 Hz, 1H), 4.81 (t, J=3.7 Hz, 1H), 4.04 (ddd, J=9.5, 6.6, 3.7 Hz, 1H), 2.57 (d, J=3.7 Hz, 1H), 2.25 (d, J=6.6 Hz, 1H); 13C NMR (125 MHz, CDCl3) δ 154.0, 139.9, 134.8, 130.9, 130.7, 130.1, 129.0, 127.8, 125.9, 122.0, 121.7, 117.0, 76.2, 71.1, 66.2; IR (film): 3407, 2919, 2851, 1583, 1485, 1455, 1239, 1036, 1012, 754, 701, 511 cm−1; LRMS (ESI): Mass calculated for [M+H]+ C15H14ClO3: 277.1; found 277.1

Workup

  1. customwas then quenched with a saturated solution of sodium thiosulfate
  2. extractionThe mixture was extracted with EtOAc
  3. washThe combined organics was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-0f06c9dc2a414c56a8b2dcb5af0f2944
Source dataset
uspto-grants-2016_04
Patent number
US09309217B2

Reaction notes

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