Aluminium lithium hydride → HCID 59814778, compound

HRID 2116726Notes

Reaction equation

HRID 2116726 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([Si:11]([CH3:26])([CH3:25])[O:12][C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[C:18]([C:22](O)=[O:23])[NH:19]2)=[CH:15][CH:14]=1)([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[C:7]([Si:11]([CH3:26])([CH3:25])[O:12][C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[C:18]([CH2:22][OH:23])[NH:19]2)=[CH:15][CH:14]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68949735HCID 68949735, compound

Product 1

HCID 59814778HCID 59814778, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1M LAH in THF (103 ml) is cooled to 0° C. A solution of 6-(tert-Butyl-dimethyl-silanyloxy)-1H-indole-2-carboxylic acid (6.0 g, 20.60 mmol) in THF (30 ml) is added slowly. The reaction is stirred at room temperature for two days, quenched with water (10 ml), 1N NaOH (10 ml) and water (20 ml). To the mixture MgSO4 is added. The mixture is filtered, washed with 10% methanol in ethyl acetate (200 ml). The filtrate is concentrated to oil. The crude is purified by column chromatography (20% ethyl acetate in hexanes) to provide [6-(tert-Butyl-dimethyl-silanyloxy)-1H-indol-2-yl]-methanol (2.30 g, 40% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.72 (s,1H) , 7.28 (d, 1H), 6.76 (s,1H), 6.50 (m,1H), 6.16 (s,1H), 5.13 (t, 1H), 4.52 (d, 2H), 0.96 (s, 9H), 0.17 (s, 6H).

Workup

  1. customquenched with water (10 ml), 1N NaOH (10 ml) and water (20 ml)
  2. additionTo the mixture MgSO4 is added
  3. filtrationThe mixture is filtered
  4. washwashed with 10% methanol in ethyl acetate (200 ml)
  5. concentrationThe filtrate is concentrated to oil
  6. customThe crude is purified by column chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-93ad0b76c3074355bb1ac967c53cf024
Source dataset
uspto-grants-2008_10
Patent number
US07439249B2

Reaction notes

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