Aluminium lithium hydride → HCID 89740116, compound

HRID 2206583Notes

Reaction equation

HRID 2206583 reaction equation
[CH3:1][C:2]([N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]1[CH3:18])([CH3:8])[C:3](OCC)=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:8][C:2]([N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]1[CH3:18])([CH3:1])[CH2:3][OH:4]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 117779051HCID 117779051, compound

Product 1

HCID 89740116HCID 89740116, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 2-methyl-2-(2-methyl-1H-indol-1-yl)propanoate (1.2 g, 4.9 mmol) in anhydrous tetrahydrofuran (10 mL) was added lithium aluminum hydride (1 g, 24.5 mmol) dissolved in anhydrous tetrahydrofuran (5 mL) dropwise between −10° C. and 0° C. After the addition, the mixture was stirred below 0° C. for 1 hour, and then allowed to stir for 3 hours at room temperature. The reaction mixture was cooled down to 0° C., quenched by 10 mL water, and then 10 mL 4N sodium hydroxide. The resulting white precipitate was filtered off, washed with acetic ester. The filtrate was dried by anhydrous sodium sulphate. The solvent was removed to afford the crude product an purified by column chromatograph on silica gel eluted with (petrol ether/acetic ester 20:1→10:1→5:1) to give 2-methyl-2-(2-methyl-1H-indol-1-yl)propan-1-ol (780 mg, 79%) as a light green oil. LCMS (M+H+) m/z: calcd. 202.14. found 202.9.

Workup

  1. additionAfter the addition
  2. stirringto stir for 3 hours at room temperature
  3. customquenched by 10 mL water
  4. filtrationThe resulting white precipitate was filtered off
  5. washwashed with acetic ester
  6. dry with materialThe filtrate was dried by anhydrous sodium sulphate
  7. customThe solvent was removed
  8. customto afford the crude product
  9. customan purified by column chromatograph on silica gel
  10. washeluted with (petrol ether/acetic ester 20:1→10:1→5:1)

Sources & evidence

ORD record
ord-dfb121d2d5b241348a17d4311ba66958
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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