Acetone → Ethyl acetate hexane

HRID 1426263Notes

Reaction equation

HRID 1426263 reaction equation
[C:1]1(C2C=CC=CC=2)[CH:6]=[CH:5][CH:4]=[C:3](C2N=C(C=O)C3C(C=2)=C[C:13]([O:17]C)=[C:12](OC)C=3)[CH:2]=1.[BH4-].[Na+].C[C:32]([CH3:34])=[O:33]>C(O)C>[CH3:12][CH2:13][O:17][C:32]([CH3:34])=[O:33].[CH3:5][CH2:6][CH2:1][CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 88546157HCID 88546157, compound

Product 1

HCID 21226206Ethyl acetate hexaneYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-([1,1′-Biphenyl]-3-yl)-6,7-dimethoxyisoquinoline-1-carboxaldehyde (160 mg) in 7 mL ethanol was treated slowly with NaBH4 (50 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 yellow solid (98 mg, 61% yield). 1H NMR (400 MHz) (CDCl3) δ 8.36-8.35 (m, 1H), 8.13-8.11 (m, 1H), 7.98 (s, 1H), 7.73 (d, J=8 Hz, 2H), 7.68-7.66 (m, 1H), 7.60 (t, J=16 Hz, 1H), 7.51 (t, J=16 Hz, 2H), 7.42 (t, J=12 Hz, 1H), 7.22 (s, 1H), 7.09 (s, 1H), 5.35 (bs, 1H), 5.32 (s, 2H), 4.08 (s, 3H), 4.07 (s, 3H). 13C NMR (100 MHz) (CDCl3) δ 154.65, 141.81, 141.21, 129.19, 128.82, 127.44, 127.29, 127.25, 125.55, 125.51, 119.82, 115.35, 105.87, 101.29, 61.41, 56.14, 56.09.

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-6409a7a260984fffa85746d65e1495ea
Source dataset
uspto-grants-2015_01
Patent number
US08933096B2

Reaction notes

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