tert-Butanol → 6-(1,2-dihydroxy-ethyl)-3-(3-methyl-isoxazol-5-yl)-4-phenyl-1H-quinolin-2-one

HRID 2053427Notes

Reaction equation

HRID 2053427 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[C:8](=[O:25])[NH:9][C:10]3[C:15]([C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:14]C(C=C)=[CH:12][CH:11]=3)[O:4][N:3]=1.S([O-])([O-])=[O:27].[Na+].[Na+].[C:32]([OH:36])([CH3:35])([CH3:34])C>>[OH:36][CH:32]([C:35]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:25])[C:7]([C:5]1[O:4][N:3]=[C:2]([CH3:1])[CH:6]=1)=[C:16]2[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:34][OH:27]

Participants

4

Reactant 3

HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 136018665HCID 136018665, compound

Product 1

HCID 1354945476-(1,2-dihydroxy-ethyl)-3-(3-methyl-isoxazol-5-yl)-4-phenyl-1H-quinolin-2-oneYield 100%

Procedure

AD-mix β was dissolved in 50% aq. tert-butanol (10 mL) followed by 3-(3-methyl-isoxazol-5-yl)-4-phenyl-6-vinyl-1H-quinolin-2-one (d) (60 mg, 0.18 mmol) and the resulting mixture was stirred at room temperature overnight. Sodium sulfite (0.3 g) was added and stirring was continued until the solution cleared. The mixture was extracted with ethyl acetate (1×20 mL, 2×10 mL) and the combined organic layers were dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography on silica gel (5% methanol in DCM) to give 6-(1,2-dihydroxy-ethyl)-3-(3-methyl-isoxazol-5-yl)-4-phenyl-1H-quinolin-2-one (e) (66 mg, 100%). 1H NMR (300 MHz, DMSO-d6) δ 12.3 (s, 1H), 7.56 (dd, J=2.6, 6.9 Hz, 1H), 7.49-7.41 (m, 3H), 7.37 (d, J=8.6 Hz, 1H), 7.27-7.18 (m, 1H), 7.09-7.04 (m, 1H), 6.41 (s, 1H), 5.25-5.20 (m, 1H), 4.65 (dd, J=6.4, 7.7Hz, 1H), 4.46-4.36 (m, 1H), 2.12 (s, 3H). MS: 363.2 (M+H).

Workup

  1. stirringstirring
  2. extractionThe mixture was extracted with ethyl acetate (1×20 mL, 2×10 mL)
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel (5% methanol in DCM)

Sources & evidence

ORD record
ord-c9a16ba7e729464e9f150e0af918f6b0
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

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