Tetrahydrofuran → HCID 86707508, compound

HRID 339007Notes

Reaction equation

HRID 339007 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[Si:49]([O:56][CH2:57][C@@H:58](O)[CH3:59])([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50]>O>[Si:49]([O:56][CH2:57][C@H:58]([O:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2)[CH3:59])([C:52]([CH3:53])([CH3:54])[CH3:55])([CH3:51])[CH3:50]

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 132242-Methyl-8-hydroxyquinolineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 13175136(S)-1-((Tert-butyldimethylsilyl)oxy)propan-2-OL

Product 1

HCID 86707508HCID 86707508, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-methylquinolin-8-ol (0.40 g, 2.5 mmol) in tetrahydrofuran (2.1 mL, 2.5 mmol) was added triphenylphosphine (1.6 g, 6.3 mmol), diethyl azodicarboxylate (0.63 mL, 4.0 mmol), and (S)-1-(tert-butyldimethylsilyloxy)propan-2-ol (0.62 g, 3.3 mmol). The resultant mixture was allowed to stir at ambient temperature for 24 hours. The reaction mixture was diluted with water (10 mL) and extracted with dichloromethane (2×20 mL). The combined organic extracts were dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by normal phase chromatography on silica gel (10-30% ethyl acetate/hexanes) to provide the title compound (0.33 g, 40%).

Workup

  1. extractionextracted with dichloromethane (2×20 mL)
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by normal phase chromatography on silica gel (10-30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c427f76ad1ce48b6aee4697a4bce6f55
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

Loading…