Water → HCID 68704626, compound

HRID 272343Notes

Reaction equation

HRID 272343 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. for 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 mixture 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-4e0d85214fc845b5b1446b43153520dc
Source dataset
uspto-grants-2008_11
Patent number
US07456162B2

Reaction notes

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