Diisobutylaluminum hydride → 3-Methyl-tridec-2e-en-1-ol

HRID 2190244Notes

Reaction equation

HRID 2190244 reaction equation
[CH3:1]/[C:2](/[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:3]\[C:4](OCC)=[O:5].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[CH3:1]/[C:2](/[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:3]\[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 58792340Ethyl 3-methyltridec-2E-enoate

Product 1

HCID 587923493-Methyl-tridec-2e-en-1-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

Compound E (0.19 mmol) was dissolved in anhydrous toluene (3 mL) and chilled to −78° C. DIBAL-H (0.585 mmol, 2.0 M in toluene) was added dropwise. The solution reacted for 45 minutes and was warmed slightly. The reaction was quenched with 10% aqueous sodium potassium tartrate. The layers were separated and the aqueous layer was extracted (3×20 mL) with ethyl acetate. The organic layers were combined, washed with brine (10 mL), dried, filtered and concentrated. Purification by flash chromatography (9:1 hexane/ethyl acetate) gave F in yields of 85-90%. 1H NMR (300 MHz, CDCl3): δ 0.8 (t, 3H), 1.25 (narrow m, 20H), 1.5 (s, 3H), 1.8 (narrow m, 2H), 4.0 (d, 2H), and 5.4 (t, 1H).

Workup

  1. customThe solution reacted for 45 minutes
  2. temperaturewas warmed slightly
  3. customThe reaction was quenched with 10% aqueous sodium potassium tartrate
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted (3×20 mL) with ethyl acetate
  6. washwashed with brine (10 mL)
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by flash chromatography (9:1 hexane/ethyl acetate)
  11. customgave F
  12. customin yields of 85-90%

Sources & evidence

ORD record
ord-22ed11987602489baf4dfc85a99a25e3
Source dataset
uspto-grants-2012_12
Patent number
US08324378B2

Reaction notes

Loading…