HCID 18988257, compound → HCID 18988286, compound

HRID 2396129Notes

Reaction equation

HRID 2396129 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH2:6][CH:7]([CH2:13][CH2:14][CH2:15][CH3:16])[C:8](OCC)=[O:9].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH2:6][CH:7]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:8][OH:9]

Participants

4

Reactant 2

HCID 18988257HCID 18988257, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18988286HCID 18988286, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Part D. A solution of the ester prepared in Part C above (4.00 g, 13.6 mmol) in tetrahydrofuran (20 mL) was added dropwise to an ice-cooled solution of lithium aluminum hydride (30 mmol) in tetrahydrofuran (30 mL).The ice bath was removed, and the mixture was warmed to ambient temperaturefor 14 hours. The solution was then recooled to 0° C., and quenched by the slow addition of 1 mL water, 3 mL 15% sodium hydroxide, and 3 mL water. The resulting mixture was filtered through a plug of celite, and the filtrate was dried over anhydrous potassium carbonate, filtered and evaporated. The residue was separated by flash chromatography (1:4 ethyl acetate-hexane) to afford the product, 2-(3,4-dimethoxybenzyl)-1-hexanol, as an oil (3.39 g, 13.4 mmol, 99%). 1H NMR (CDCl3): δ 6.81-6.70 (3H, m); 3.87 (3H, s); 3.86 (3H, s); 3.54 (2 H, t, J=5.1 Hz); 2.59 (2H, d, J=7.0 Hz); 1.80-1.71 (1H, m); 1.39-1.17 (7H, m); 0.89 (3H, t,J=7.0 Hz). Mass spectrum (NH3 -CI/DDIP): m/z 254 (5%); 253 (33%); 235 (100%); 151 (43%).

Workup

  1. customice bath was removed
  2. temperaturethe mixture was warmed
  3. customwas then recooled to 0° C.
  4. customquenched by the slow addition of 1 mL water, 3 mL 15% sodium hydroxide, and 3 mL water
  5. filtrationThe resulting mixture was filtered through a plug of celite
  6. dry with materialthe filtrate was dried over anhydrous potassium carbonate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was separated by flash chromatography (1:4 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-2d5bd25dc7a5424ea67387afffa69b36
Source dataset
uspto-grants-1996_02
Patent number
US05491152

Reaction notes

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