Diisobutylaluminum hydride → HCID 14022229, compound

HRID 9806Notes

Reaction equation

HRID 9806 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[C:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[C:9]1(=[CH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][OH:2])[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 140222256-Cyclopentylidene-hexanoic acid methyl ester

Product 1

HCID 14022229HCID 14022229, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 6-cyclopentylidene-hexanoic acid methyl ester (2.77 g, 14.1 mmol) in toluene (130 mL) was added DIBAL-H (35.3 mL, 1 M solution in hexane, 35.3 mmol) dropwise at 0° C. under N2. After sting at 0° C. for 30 min, the reaction was quenched by MeOH (10 mL). Saturated aqueous sodium potassium tartrate (80 mL) was added to the reaction mixture. After stirring for 1 h, the organic layer was separated and the aqueous phase was extracted with ether. The combined organic layers were washed with water and brine and dried. Evaporation of the solvent gave 6-cyclopentylidene-hexan-1-ol (2.47 g, 98%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 5.24 (1H, m), 3.63 (2H, t, J=6.6 Hz), 2.21 (4H, m), 1.97 (2H, m), 1.50–1.70 (6H, m), 1.34 (2H, m); 13C NMR (75 MHz, CDCl3) δ 143.28, 120.08, 63.22, 33.82, 33.00, 29.81, 29.75, 28.87, 26.72, 26.63, 25.73.

Workup

  1. customthe reaction was quenched by MeOH (10 mL)
  2. additionSaturated aqueous sodium potassium tartrate (80 mL) was added to the reaction mixture
  3. customthe organic layer was separated
  4. extractionthe aqueous phase was extracted with ether
  5. washThe combined organic layers were washed with water and brine
  6. customdried
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-1031d7c9f29c406cb2da0b969215688a
Source dataset
uspto-grants-2006_08
Patent number
US07091357B2

Reaction notes

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