Water → HCID 68704626, compound

HRID 272307Notes

Reaction equation

HRID 272307 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]([CH3:17])[C:12](OCC)=[O:13])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Cl-].[Ce+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]=[C:11]([CH3:17])[CH2:12][OH:13])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24636Cerium(III) chlorideHCID 21226445Aluminium lithium hydrideHCID 68704703Ethyl 3-(4-isopropylphenyl)-2-methyl-2-propenoate

Product 1

HCID 68704626HCID 68704626, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of ethyl 3-(4-isopropylphenyl)-2-methyl-2-propenoate (9.00 g, 38.7 mmol) and cerium chloride (1.00 g, 4.06 mmol) in tetrahydrofuran (50 ml) was added in four portions at −40° C. over a period of 30 minutes lithium aluminum hydride (1.47 g, 38.7 mmol) and the resulting mixture was stirred at the same temperature for 30 minutes. Water was added into the reaction solution and the product was extracted twice with ethyl acetate. The combined extracts were washed with water, dried on magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel (hexane-ethyl acetate 8:1) to obtain 6.30 g (86% yield) of the oily title compound.

Workup

  1. extractionthe product was extracted twice with ethyl acetate
  2. washThe combined extracts were washed with water
  3. customdried on magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-97c1c92e4bc34ce0963d6da4f3047eb9
Source dataset
uspto-grants-2008_11
Patent number
US07456162B2

Reaction notes

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