Aluminium lithium hydride → HCID 21639277, compound

HRID 2095392Notes

Reaction equation

HRID 2095392 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][C:8](OCCCC)=[O:9])=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[NH:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][CH2:8][OH:9])=[CH:2]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67317933HCID 67317933, compound

Product 1

HCID 21639277HCID 21639277, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of butyl 3-(1H-pyrrol-3-yl)propionate (14.1 g, 72.3 mmol) in ether (400 mL) was added LiAlH4 (4.12 g, 108 mmol, 1.50 equiv.) at 0° C. under N2. The solution was stirred for 2 h at 0° C., and the reaction was cautiously quenched with saturated aqueous NH4Cl. The resulting solution was extracted with ether (3×150 mL). The combined organic layers were dried and concentrated under vacuum to give 3-(1H-pyrrol-3-yl)-1-propanol (8.0 g, 89%) as a light-yellow oil. 1H NMR (CDCl3, 300 MHz) δ 8.11 (br, 1H), 6.76 (s, 1H), 6.63 (s, 1H), 6.14 (s, 1H), 3.73 (t, 2H, J=6.6 Hz), 2.62 (t, 2H, J=7.5 Hz), 1.85-1.94 (m, 2H). LC-MS (ESI) m/z 126 (M+H+).

Workup

  1. customthe reaction was cautiously quenched with saturated aqueous NH4Cl
  2. extractionThe resulting solution was extracted with ether (3×150 mL)
  3. customThe combined organic layers were dried
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f71be808708d4aaab856a4fee3466475
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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