Tetrahydrofuran → 2-(1,2-dihydroxyethyl)-7,8-dihydroquinolin-5(6H)-one

HRID 1506410Notes

Reaction equation

HRID 1506410 reaction equation
C(C1C=C[C:10]2[C:9](=[O:13])[CH2:8][CH2:7][CH2:6][C:5]=2N=1)=C.C[N+:15]1([O-])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C1C[O:25][CH2:24]C1>C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[OH:18][CH:19]([C:20]1[CH:6]=[CH:7][C:8]2[C:9](=[O:13])[CH2:10][CH2:5][CH2:17][C:16]=2[N:15]=1)[CH2:24][OH:25]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 671675322-vinyl-7,8-dihydroquinolin-5(6H)-one

Product 1

HCID 671713442-(1,2-dihydroxyethyl)-7,8-dihydroquinolin-5(6H)-oneYield 47%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-vinyl-7,8-dihydroquinolin-5(6H)-one (Preparation 54C, 0.400 g, 2.31 mmol) and N-methylmorpholine-N-oxide (50% in water, 0.479 mL, 2.31 mmol) in THF (11 mL) at room temperature was added osmium tetroxide (4% in water, 0.725 mL, 0.092 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with water (50 mL). The organic layer was washed with brine (50 mL), the combined aqueous layers were extracted with ethyl acetate (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 2-(1,2-dihydroxyethyl)-7,8-dihydroquinolin-5(6H)-one (0.226 g, 1.09 mmol, 47% yield) as a yellow oil. The compound had an HPLC ret. time=0.330 min. (condition A); LC/MS M+1=207.9.

Workup

  1. washwashed with water (50 mL)
  2. washThe organic layer was washed with brine (50 mL)
  3. extractionthe combined aqueous layers were extracted with ethyl acetate (100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2e65ca4a69b3436aa34c3a5ac0e6f48d
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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