Water → HCID 18184657, compound

HRID 1358493Notes

Reaction equation

HRID 1358493 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH2:11][CH2:12][C:13](OCC)=[O:14].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH2:11][CH2:12][CH2:13][OH:14]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 18184582HCID 18184582, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18184657HCID 18184657, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of ethyl 3-(1-methylindol-2-yl)propionate (2.0 g, 8.65 mmol) in tetrahydrofuran (20 ml) was added lithium aluminum hydride (328 mg, 8.65 mmol) by small portions under nitrogen atmosphere. After the mixture was stirred for 1 hour, water and aqueous 15% sodium hydroxide solution were added successively to the mixture. The resulting precipitates were filtrated off through Celite and washed with tetrahydrofuran. The filtrate was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel (36 g) chromatography eluting with dichloromethane-methanol (100:1 to 50:1) to give 3-(1-methylindol-2-yl)propan-1-ol (1.05 g, 64.1%) as a yellow syrup.

Workup

  1. customThe resulting precipitates
  2. filtrationwere filtrated off through Celite
  3. washwashed with tetrahydrofuran
  4. dry with materialThe filtrate was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel (36 g) chromatography
  7. washeluting with dichloromethane-methanol (100:1 to 50:1)

Sources & evidence

ORD record
ord-5e49ec9e44e2437faf95817800668e22
Source dataset
uspto-grants-2003_07
Patent number
US06596738B1

Reaction notes

Loading…