Acetone → Ethyl acetate hexane

HRID 1426261Notes

Reaction equation

HRID 1426261 reaction equation
[C:1]([C:5]1C=C(C2C=CC=C(C3N=C(C=O)C4C(C=3)=C[C:23]([O:27]C)=[C:22](OC)C=4)C=2)[CH:8]=[CH:9][CH:10]=1)(C)(C)[CH3:2].[BH4-].[Na+].C[C:36]([CH3:38])=[O:37]>C(O)C>[CH3:22][CH2:23][O:27][C:36]([CH3:38])=[O:37].[CH3:2][CH2:1][CH2:5][CH2:10][CH2:9][CH3:8]

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 86683786HCID 86683786, compound

Product 1

HCID 21226206Ethyl acetate hexaneYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(3′-(tert-Butyl)-[1,1′-biphenyl]-3-yl)-6,7-dimethoxyisoquinoline-1-carbaldehyde (52 mg) in 4 mL ethanol was treated slowly with NaBH4 (14 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 oil (27 mg, 52% yield). 1H NMR (400 MHz) (CDCl3) δ 8.24 (t, J=4 Hz, 1H), 8.03-8.01 (m, 1H), 7.88 (s, 1H), 7.62 (m, 1H), 7.57-7.55 (m, 1H), 7.51 (t, J=12 Hz, 1H), 7.45-7.42 (m, 1H), 7.36-7.35 (m, 2H), 7.12 (s, 1H), 6.98 (s, 1H), 5.39 (bs, 1H), 5.12 (s, 2H), 3.99 (s, 3H), 3.98 (s, 3H), 1.33 (s, 9H). 13C NMR (100 MHz) (CDCl3) δ 154.60, 153.16, 151.69, 150.40, 147.62, 142.51, 141.06, 139.64, 133.80, 129.14, 128.55, 127.49, 125.67, 125.47, 124.61, 124.52, 124.46, 119.79, 115.38, 105.87, 101.22, 61.39, 56.13, 34.88, 31.47.

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-949bcc6dcf74418fad63de078c877b9c
Source dataset
uspto-grants-2015_01
Patent number
US08933096B2

Reaction notes

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