Diethyl Ether → HCID 67076299, compound

HRID 1810909Notes

Reaction equation

HRID 1810909 reaction equation
[OH:1][C:2]([CH3:15])([CH3:14])[CH2:3][C:4]1[CH:5]=[C:6]([CH2:10][C:11](O)=[O:12])[CH:7]=[CH:8][CH:9]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.CC(=O)OCC>C1COCC1.O>[OH:12][CH2:11][CH2:10][C:6]1[CH:5]=[C:4]([CH2:3][C:2]([CH3:15])([OH:1])[CH3:14])[CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 46938719[3-(2-Hydroxy-2-methylpropyl)phenyl]acetic acid

Product 1

HCID 67076299HCID 67076299, compoundYield 39.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The compound of step 1 (0.132 g, 0.634 mmol) was dissolved in THF (0.5 ml) and added to a refluxing suspension of lithium aluminium hydride (122 mg, 3.1 mmol) in THF (1 ml). The mixture was stirred for 1 h under reflux and cooled to room temperature. Diethyl ether (6 ml) was added, followed by EA (0.4 ml). Subsequently, water was added slowly until the alumina salts formed a thick slurry from which the supernatant could be decanted easily. The slurry was repeatedly washed with EA, the combined extracts were dried with sodium sulfate and evaporated to dryness. The residue was purified by RP HPLC (water/ACN gradient) to yield 49 mg of the title compound.

Workup

  1. temperatureunder reflux
  2. customformed a thick slurry from which the supernatant
  3. customcould be decanted easily
  4. washThe slurry was repeatedly washed with EA
  5. dry with materialthe combined extracts were dried with sodium sulfate
  6. customevaporated to dryness
  7. customThe residue was purified by RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-ce89ab0eebd249e89dd3e0b509ecedf1
Source dataset
uspto-grants-2013_01
Patent number
US08362073B2

Reaction notes

Loading…