Tetrahydrofuran → HCID 87331335, compound

HRID 251734Notes

Reaction equation

HRID 251734 reaction equation
[CH2:1]([C:3]1([CH2:8][CH2:9][CH2:10][CH2:11][C:12](N(OC)C)=[O:13])[O:7][CH2:6][CH2:5][O:4]1)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:24]1COCC1>>[CH2:1]([C:3]1([CH:8]([CH3:24])[CH2:9][CH2:10][CH2:11][CH:12]=[O:13])[O:4][CH2:5][CH2:6][O:7]1)[CH3:2]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 87331788HCID 87331788, compound

Product 1

HCID 87331335HCID 87331335, compound

Procedure

To a stirred mixture of 5-(2-ethyl-1,3-dioxolan-2-yl)-N-methoxy-N-methyl-pentanamide (1 eq.) [Prepared by coupling 7-oxononanoic acid with N, O-dimethylhydroxylamine and subsequent ketal protection] in anhydrous THF at −78° C. was added a 1 M LiAlH4 solution in THF (1.6 eq.) slowly over 5 min. After 45 min the reaction was quenched by addition of Et2O and then aq. Rochelle's salt solution (10% w/v). The mixture was warmed to RT with a vigourous stirring. The organic phase was separated, washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 5% EtOAc/Petroleum ether to afford the desired aldehyde. 1H NMR (300 MHz, CD3CN) δ: 9.77 (1H, s), 4.00 (4H, s), 2.44 (2H, t, J=7.0 Hz), 1.75-1.48 (6H, m), 1.46-1.25 (4H, m), 1.00-0.80 (3H, t, J=7.0 Hz).

Workup

  1. customAfter 45 min the reaction was quenched by addition of Et2O
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography
  7. washeluting with 5% EtOAc/Petroleum ether

Sources & evidence

ORD record
ord-6ff818ff2f0b436c8436974ce9817e45
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Reaction notes

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