Ethyl Acetate → HCID 18546297, compound

HRID 1267488Notes

Reaction equation

HRID 1267488 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:27][CH:28]=[CH2:29])[C:10]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][O:25][CH3:26])=[CH:19][CH:18]=3)([CH3:16])[C:11](=[O:15])[O:12]2)=[CH:7][CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[Cl-].[NH4+]>O1CCCC1>[OH:12][C:13]1[CH:14]=[C:5]([O:4][CH2:3][O:2][CH3:1])[CH:6]=[CH:7][C:8]=1[CH:9]([CH2:27][CH:28]=[CH2:29])[C:10]([C:17]1[CH:18]=[CH:19][C:20]([O:23][CH2:24][O:25][CH3:26])=[CH:21][CH:22]=1)([CH3:16])[CH2:11][OH:15]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 18546294HCID 18546294, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18546297HCID 18546297, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methyl-4-(2-propenyl)chroman-2-one (6.91 g) in anhydrous tetrahydrofuran (26 ml) was added dropwise to an ice-cold suspension of lithium aluminum hydride (1.65 g) in anhydrous tetrahydrofuran (50 ml) over 20 minutes under nitrogen atmosphere, and the reaction mixture was then stirred on ice for 50 minutes. Ethyl acetate (20 ml) and saturated aqueous ammonium chloride (20 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)-3-(2-hydroxy-4-methoxymethoxyphenyl)-2-(4-methoxymethoxyphenyl)-2-methyl-5-hexen-1-ol (6.94 g, Yield 99.4%) 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-ac9e7135afaa486b849661d8f7994ddc
Source dataset
uspto-grants-2003_04
Patent number
US06552069B1

Reaction notes

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