Acetone → Ethyl acetate hexane

HRID 1426266Notes

Reaction equation

HRID 1426266 reaction equation
[C:1]([C:5]1C=C(C2N=C(C=O)C3C(C=2)=C[C:17]([O:21]C)=[C:16](OC)C=3)[CH:8]=[CH:9][CH:10]=1)(C)(C)[CH3:2].[BH4-].[Na+].C[C:30]([CH3:32])=[O:31]>C(O)C>[CH3:16][CH2:17][O:21][C:30]([CH3:32])=[O:31].[CH3:2][CH2:1][CH2:5][CH2:10][CH2:9][CH3:8]

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 88545915HCID 88545915, compound

Product 1

HCID 21226206Ethyl acetate hexaneYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(3-(tert-Butyl)phenyl)-6,7-dimethoxyisoquinoline-1-carboxaldehyde (97 mg) in 5 mL ethanol was treated slowly with NaBH4 (26 mg, 3 eq.) at room temperature. Reaction was stirred for 1 hour then 2 mL acetone was added and solution was filtered through filter paper. Filtrate was concentrated then re-dissolved in DCM and washed with H2O. Organic layer was dried over sodium sulfate and concentrated. Chromatography achieved using ISCO max gradient 50% EtOAc/hexane yielding product as a pale yellow solid (50 mg, 63% yield). 1H NMR (400 MHz) (CDCl3) δ 8.07 (m, 1H), 7.86-7.83 (m, 1H), 7.82 (s, 1H), 7.39-7.37 (m, 2H), 7.13 (s, 1H), 6.98 (s, 1H), 5.12 (s, 2H), 3.99 (s, 3H), 3.98 (s, 3H), 1.35 (s, 9H). 13C NMR (100 MHz) (CDCl3) δ 154.47, 153.14, 151.62, 150.31, 148.21, 138.90, 133.85, 128.51, 125.55, 123.97, 123.65, 119.64, 115.25, 105.84, 101.22, 61.32, 56.13, 56.10, 34.90, 31.45. IR (thin film NaCl) 3345, 2957, 1621, 1577, 1506, 1467, 1416, 1362, 1276, 1247, 1163, 1090, 1023, 991, 874, 834, 800, 701.

Workup

  1. customReaction
  2. filtrationsolution was filtered
  3. filtrationthrough filter paper
  4. concentrationFiltrate was concentrated
  5. dissolutionthen re-dissolved in DCM
  6. washwashed with H2O
  7. dry with materialOrganic layer was dried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6a325073bfce4786aabe9832d0e877d3
Source dataset
uspto-grants-2015_01
Patent number
US08933096B2

Reaction notes

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