Aluminium lithium hydride → HCID 59678648, compound

HRID 1751829Notes

Reaction equation

HRID 1751829 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=[CH:6][CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.O>[Si:15]([O:14][CH2:13][CH2:12][O:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[CH:5][CH:6]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 596786884-[2-(t-Butyldimethylsilanyloxy)ethoxymethyl]benzoic acid methyl ester

Product 1

HCID 59678648HCID 59678648, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Example 5B (670 mg, 2.18 mmol) dissolved in anhydrous THF (22 mL) was added a solution of LAH (1.0 M solution in THF, 2.18 mL, 2.18 mmol) dropwise. After completion of addition the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with water. The aqueous layer was extracted with ethyl acetate (3×). All combined organic layers were dried over Na2SO4, filtered, and concentrated to provide an oil (587 mg, 1.98 mmol), which was used in the next step without any further purification (91% yield).

Workup

  1. additionAfter completion of addition the reaction mixture
  2. extractionThe aqueous layer was extracted with ethyl acetate (3×)
  3. dry with materialAll combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b00c8b9add244509bc345d70e3205f58
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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