Ethyl Acetate → HCID 18546255, compound

HRID 1267769Notes

Reaction equation

HRID 1267769 reaction equation
[CH2:1]([C:3]1([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][O:29][CH3:30])=[CH:23][CH:22]=2)[CH:12]([CH2:13][CH:14]=[CH2:15])[C:11]2[C:6](=[CH:7][C:8]([O:16][CH2:17][O:18][CH3:19])=[CH:9][CH:10]=2)[O:5][C:4]1=[O:20])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([C:3]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][O:29][CH3:30])=[CH:23][CH:22]=1)([CH:12]([C:11]1[CH:10]=[CH:9][C:8]([O:16][CH2:17][O:18][CH3:19])=[CH:7][C:6]=1[OH:5])[CH2:13][CH:14]=[CH2:15])[CH2:4][OH:20])[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 18546280HCID 18546280, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18546255HCID 18546255, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (3RS,4RS)-3-ethyl-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-4-(2-propenyl)chroman-2-one (9.4 g) in dry tetrahydrofuran (50 ml) was added dropwise to an ice-cold suspension of lithium aluminum hydride (2.2 g) in dry tetrahydrofuran (50 ml) over 25 minutes under nitrogen atmosphere, and the reaction mixture was then stirred on ice for 1 hour and 15 minutes. Ethyl acetate (30 ml) and saturated aqueous ammonium chloride (30 ml) were added to stop the reaction, followed by stirring for 1 hour at room temperature. The reaction mixture was filtered through cellite and the resulting filtrate was extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous ammonium chloride, dried over magnesium sulfate, and then concentrated under reduced pressure to give (2RS,3RS)-2-ethyl-3-(2-hydroxy-4-methoxymethoxyphenyl)-2-(4-methoxymethoxyphenyl)-5-hexenol (9.5 g, quantitative) as a crude product, which was then used for the subsequent reaction without further purification.

Workup

  1. customthe reaction
  2. stirringby stirring for 1 hour at room temperature
  3. filtrationThe reaction mixture was filtered through cellite
  4. extractionthe resulting filtrate was extracted twice with ethyl acetate
  5. washThe combined organic layers were washed with saturated aqueous ammonium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-61ff3241142845298081d03ffcc2b5c5
Source dataset
uspto-grants-2003_04
Patent number
US06552068B1

Reaction notes

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