Diisobutylaluminum hydride → 66505-81-5

HRID 1245412Notes

Reaction equation

HRID 1245412 reaction equation
CC(C[AlH]CC(C)C)C.C[O:11][C:12](=O)[CH:13]=[C:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>C(Cl)Cl>[O:17]1[CH2:18][CH2:19][C:14](=[CH:13][CH2:12][OH:11])[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 54595149Methyl (oxan-4-ylidene)acetate

Product 1

HCID 1098624366505-81-5Yield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

DIBAL 1 M in methylene chloride (76.9 mL, 76.9 mmol) was added to a solution of (tetrahydro-pyran-4-ylidene)-acetic acid methyl ester (4.0 g, 25.6 mmol) in methylene chloride (100 mL) under nitrogen atmosphere cooled to −78° C. The reaction was stirred for 1 h, allowed to warm to room temperature, and stirred for an additional 2 h. The reaction was cooled to 0° C. and slowly quenched with methanol (35 mL). The reaction was vigorously stirred with water (35 mL) and Na2SO4 (170 g) for 30 minutes at room temperature. The resulting slurry was filtered and concentrated to give 2-(tetrahydro-pyran-4-ylidene)-ethanol (3.2 g, 97%) as a colorless oil.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for an additional 2 h
  3. temperatureThe reaction was cooled to 0° C.
  4. customslowly quenched with methanol (35 mL)
  5. stirringThe reaction was vigorously stirred with water (35 mL) and Na2SO4 (170 g) for 30 minutes at room temperature
  6. filtrationThe resulting slurry was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-22e7f3cd857e484b9155507fb642a633
Source dataset
uspto-grants-2006_10
Patent number
US07125870B2

Reaction notes

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