Diisobutylaluminumhydride → HCID 68697080, compound

HRID 2236683Notes

Reaction equation

HRID 2236683 reaction equation
C[O:2][C:3]([C:5]1[CH:15]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:8]2[O:9][C:10]([CH3:13])([CH3:12])[O:11][C:7]=2[CH:6]=1)=O.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[CH2:17]([O:16][C:14]1[C:8]2[O:9][C:10]([CH3:12])([CH3:13])[O:11][C:7]=2[CH:6]=[C:5]([CH2:3][OH:2])[CH:15]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 21225700Diisobutylaluminumhydride2×HCID 68695848HCID 68695848, compound

Product 1

HCID 68697080HCID 68697080, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A −78° C. solution of 7-benzyloxy-2,2-dimethyl-benzo[1,3]dioxole-5-carboxylic acid methyl ester (0.62 g, 2.0 mmol) in toluene (17 mL) is treated with di-isobutylaluminum hydride (1.0 M solution I hexanes, 4.4 mL, 4.4 mmol), which is added dropwise over 15 minutes. After 5 minutes of stirring, the reaction is quenched by the addition of 10% aqueous hydrochloric acid solution. After warming to room temperature, the mixture is extracted 3× with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to provide (7-benzyloxy-2,2-dimethyl-benzo[1,3]dioxol-5-yl)-methanol in quantitative yield.

Workup

  1. additionis added dropwise over 15 minutes
  2. customthe reaction is quenched by the addition of 10% aqueous hydrochloric acid solution
  3. extractionthe mixture is extracted 3× with ethyl acetate
  4. washThe combined extracts were washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-04dfd6c5fc0c42afb7fb2eee3dd7bb6e
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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