Aluminium lithium hydride → HCID 57890220, compound

HRID 1819969Notes

Reaction equation

HRID 1819969 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:11]([C:16]2[CH:21]=[CH:20][C:19]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[C:18]([CH3:30])[CH:17]=2)([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:8][C:9]=1[CH3:10])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:26]([Si:23]([CH3:25])([CH3:24])[O:22][C:19]1[CH:20]=[CH:21][C:16]([C:11]([C:7]2[S:6][C:5]([CH2:3][OH:2])=[C:9]([CH3:10])[CH:8]=2)([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:17][C:18]=1[CH3:30])([CH3:28])([CH3:27])[CH3:29]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57890086HCID 57890086, compound

Product 1

HCID 57890220HCID 57890220, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 5-{1-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-phenyl]-1-ethyl-propyl}-3-methyl-thiophene-2-carboxylic acid methyl ester (10.0 g, 22.39 mmol) in THF (200 ml) is added portionwise lithium aluminum hydride (1.70 g, 44.78 mmol) and the reaction mixture is warmed to RT for 1 h. The reaction is quenched with water (1.7 ml), 5N NaOH (1.7 ml), and water (5.1 ml). The reaction mixture is filtered, concentrated and chromatographed (120 g SiO2, 10% EtOAc/Hex) to yield the title compound (7.0 g, 75%).

Workup

  1. customThe reaction is quenched with water (1.7 ml), 5N NaOH (1.7 ml), and water (5.1 ml)
  2. filtrationThe reaction mixture is filtered
  3. concentrationconcentrated
  4. customchromatographed (120 g SiO2, 10% EtOAc/Hex)

Sources & evidence

ORD record
ord-3c7eb3a0a709414daf5b03a986e7251d
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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