Diethyl Ether → HCID 67076611, compound

HRID 2405259Notes

Reaction equation

HRID 2405259 reaction equation
C[O:2][C:3](=O)[C:4]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][C:17](OC)=[O:18])[CH:11]=1)([CH3:9])[C:5](OC)=[O:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.CC(=O)OCC>C1COCC1.O>[OH:18][CH2:17][CH2:16][C:12]1[CH:11]=[C:10]([C:4]([CH3:9])([CH2:3][OH:2])[CH2:5][OH:6])[CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 67076719HCID 67076719, compound

Product 1

HCID 67076611HCID 67076611, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The compound of step 2 (0.128 g, 0.435 mmol) was dissolved in 2 ml of THF and cautiously added to an ice-cold suspension of lithium aluminium hydride (174 mg, 4.35 mmol) in THF. After a few minutes, diethyl ether (12 ml) was added and thereafter 200 μl of EA. Subsequently, water was added slowly and cautiously until the alumina salts formed a light grey mass at the bottom of the flask. The supernatant was decanted and the residue washed with EA. The combined extracts were dried over sodium sulfate and evaporated to dryness. The residue was used in the next step without further purification.

Workup

  1. waitAfter a few minutes
  2. customformed a light grey mass at the bottom of the flask
  3. customThe supernatant was decanted
  4. washthe residue washed with EA
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. customevaporated to dryness
  7. customThe residue was used in the next step without further purification

Sources & evidence

ORD record
ord-ee84655d0c974739bedfb05c1341c9d9
Source dataset
uspto-grants-2014_08
Patent number
US08802720B2

Reaction notes

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