Tetrahydrofuran → HCID 21510684, compound

HRID 1576479Notes

Reaction equation

HRID 1576479 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=O)[C:11]([N:13]2[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14]2)=O)=[CH:2]1.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O>[OH:18][CH:15]1[CH2:16][CH2:17][N:13]([CH2:11][CH2:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[CH2:14]1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 21510699HCID 21510699, compound

Product 1

HCID 21510684HCID 21510684, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 11 g. (0.043 mole) of 1-(indol-3-ylglyoxyloyl)-3-pyrrolidinol in 50 ml. of tetrahydrofuran was added dropwise, under nitrogen, to a stirred suspension of 9.8 g. (0.026 mole) of lithium aluminum hydride in 100 ml. of tetrahydrofuran. After addition, the mixture was refluxed for 2 hours, cooled, and treated with enough water to destroy the excess lithium aluminum hydride. The resulting aluminum hydroxide was filtered off and washed thoroughly with tetrahydrofuran. The filtrate was evaporated on a rotating evaporator to an oil which solidified on standing. Crystallization from acetonitrile gave a melting point of 144°-146° C.; yield 7.7 g. (78%).

Workup

  1. additionA suspension of 11 g
  2. additionAfter addition
  3. temperaturethe mixture was refluxed for 2 hours
  4. temperaturecooled
  5. customto destroy the excess lithium aluminum hydride
  6. filtrationThe resulting aluminum hydroxide was filtered off
  7. washwashed thoroughly with tetrahydrofuran
  8. customThe filtrate was evaporated on a rotating evaporator to an oil which
  9. customCrystallization from acetonitrile
  10. customgave a melting point of 144°-146° C.

Sources & evidence

ORD record
ord-1ec59fd4ea634c82a28e8f5a2db2409c
Source dataset
uspto-grants-1976_09
Patent number
USRE028973

Reaction notes

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