Aluminium lithium hydride → HCID 86653887, compound

HRID 1692186Notes

Reaction equation

HRID 1692186 reaction equation
CC(C(=C)CC(C)C)CO.[CH2:11]([CH:13]([C:19](=[CH2:24])[CH2:20][CH:21]([CH3:23])[CH3:22])[C:14](OCC)=[O:15])[CH3:12].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:11]([CH:13]([C:19](=[CH2:24])[CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:14][OH:15])[CH3:12]

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 86653885HCID 86653885, compoundHCID 86653888HCID 86653888, compound2×

Product 1

HCID 86653887HCID 86653887, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As described for preparation of 2,5-dimethyl-3-methylenehexan-1-ol (vide supra), from ethyl 2-ethyl-5-methyl-3-methylenehexanoate (26.8 g, 135 mmol) and LAH (5.12 g, 135 mmol) in THF (500 mL) the 2-ethyl-5-methyl-3-methylenehexan-1-ol (17.5 g, 83%) was obtained as a colourless odoriferous liquid after standard workup and purification by silica-gel flash chromatography (pentane/Et2O, 8:2, Rf=0.18). IR (neat): ν=3332 (s, ν O—H), 1463 (w, δas CH3), 1365 (w, δs, CH3), 1034 (s, ν C—O), 892 (s, δ C═H) cm−1. 1H NMR (CDCl3): δ=0.88 (t, J=7.5 Hz, 3H, 2′-CH3), 0.91 (d, J=6.5 Hz, 6H, 5-Me2), 1.38-1.49 (m, 2H, 1′-H2), 1.77 (br. s, 1H, OH), 1.78-1.83 (m, 1H, 5-H), 1.85-1.89 (m, 2H, 4-H2), 2.11 (quint, J=8.0 Hz, 1H, 2-H), 3.51-3.55 (m, 2H, 1-H2), 4.86 (d, J=1.5 Hz, 1H, 1′-HE), 4.92 (d, J=1.5 Hz, 1H, 1′-HZ) ppm. 13C NMR (CDCl3): δ=11.7 (q, C-2′), 22.4/22.7 (2q, 5-Me2), 22.9 (t, C-1′), 25.8 (d, C-5), 44.5 (t, C-4), 49.7 (d, C-2), 64.2 (t, C-1), 111.7 (d, C-1″), 148.3 (s, C-3) ppm. MS (EI): m/z (%)=156 (3) [M+], 142 (2) [M+-CH3], 125 (7) [M+-CH3O], 83 (100) [C6H11+], 69 (100) [C5H9+], 43 (31) [C3H7+]. Odour description: pleasant and fresh green-floral note with spicy undertones and a natural agrestic aspects, somewhat reminiscent of beetroot with a slightly earthy twist.

Workup

  1. customwas obtained as a colourless odoriferous liquid
  2. customafter standard workup and purification by silica-gel flash chromatography (pentane/Et2O, 8:2, Rf=0.18)

Sources & evidence

ORD record
ord-ff435a68c53544ec9b71eb601885a0e9
Source dataset
uspto-grants-2012_04
Patent number
US08153848B2

Reaction notes

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