Diisobutylaluminum hydride → HCID 86707577, compound

HRID 2279971Notes

Reaction equation

HRID 2279971 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)[CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[CH:11]=1.CC(C[AlH]CC(C)C)C>C1COCC1.C1(C)C=CC=CC=1>[OH:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=2)[CH:9]=[C:8]([C:19]2[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 86707578HCID 86707578, compound

Product 1

HCID 86707577HCID 86707577, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.90 g (8.32 mmol) 3-(4,4″-dihydroxy-[1,1′;3′,1″]terphenyl-5′-yl)-propionic acid methyl ester are dissolved in THF, and 55 ml (55 mmol) of a 1 M solution of DIBAL-H in toluene are added dropwise under cooling. The cooling is removed and the mixture is stirred overnight at RT. After addition of 3 ml isopropanol the mixture is poured onto ice/water, acidified with 2 M hydrochloric acid and extracted three times with MTB ether. The combined organic layers are washed with sat. aq. sodium chloride solution and dried over sodium sulfate. The solvent is removed in vacuo and the residue is filtered through silica gel with toluene/ethylacetate (2:1). 5′-(3-hydroxy-propyl)-[1,1′;3′,1″]terphenyl-4,4″-diol is obtained as colourless solid.

Workup

  1. temperatureunder cooling
  2. customThe cooling is removed
  3. additionAfter addition of 3 ml isopropanol the mixture
  4. additionis poured onto ice/water
  5. extractionextracted three times with MTB ether
  6. washThe combined organic layers are washed with sat. aq. sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. customThe solvent is removed in vacuo
  9. filtrationthe residue is filtered through silica gel with toluene/ethylacetate (2:1)

Sources & evidence

ORD record
ord-a291f2c7219748459f6cdd3508ab89ae
Source dataset
uspto-grants-2015_09
Patent number
US09133395B2

Reaction notes

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