Water → HCID 20523236, compound

HRID 223262Notes

Reaction equation

HRID 223262 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]([CH3:17])C(OCC)=O)=[CH:8][CH:7]=[CH:6][CH:5]=2.O1CCC[CH2:19]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH2:29]>>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]([OH:29])[CH2:17][CH3:19])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 86738586HCID 86738586, compound

Product 1

HCID 20523236HCID 20523236, compoundYield 68.8%

Procedure

A solution of 27.3 g of ethyl (2-methylindol-3-yl)propionate and 100 ml of tetrahydrofuran was added slowly to a suspension of 4.3 g of lithium aluminum hydride and 120 ml of tetrahydrofuran, with stirring. After the addition was complete, the reaction mixture was heated under reflux for 2 hrs, and cooled in an ice bath. Water (17 ml) was added cautiously at ice-bath temperature. The mixture was filtered and the filtrated was concentrated. Distillation of the residue at 0.2 mm gave 15.6 g (68.8%) of product, bp 180°.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for 2 hrs
  4. temperaturecooled in an ice bath
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrated was concentrated
  7. distillationDistillation of the residue at 0.2 mm

Sources & evidence

ORD record
ord-4c0640140910493bb53f97c0315cc496
Source dataset
uspto-grants-1982_10
Patent number
US04352811

Reaction notes

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