Ethyl Acetate → HCID 12878332, compound

HRID 224429Notes

Reaction equation

HRID 224429 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9](=O)[CH2:10][C:11]1[CH:16]=[C:15]([Cl:17])[C:14]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:13][C:12]=1[O:24][CH3:25].C(OCC)(=O)C>O1CCCC1>[Cl:17][C:15]1[C:14]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:13][C:12]([O:24][CH3:25])=[C:11]([CH2:10][CH2:9][OH:8])[CH:16]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 12878331HCID 12878331, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12878332HCID 12878332, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7 g of LiAlH4 are added in portions at 0° under an inert gas atmosphere to 16 g of (5-chloro-4- cyclohexyl-2-methoxyphenyl)-acetic acid methyl ester in 350 ml of dry tetrahydrofuran. Stirring is then effected for 18 hours at 22° . 20 ml of ethyl acetate are carefully added in drops so as to destroy the excess LiAlH4. The mixture is then poured onto a solution of NH4Cl in ice water, acidified with 2N H2SO4 and extracted three times with acetic ester. The organic phases are washed with water, dried over Na2SO4 and concentrated. The residue is chromatographed on 250 g of silica gel. The product, which is extracted with methylene chloride, is distilled in a bulb tube. M.p. 78°-79°.

Workup

  1. customto destroy the excess LiAlH4
  2. additionThe mixture is then poured onto a solution of NH4Cl in ice water
  3. extractionextracted three times with acetic ester
  4. washThe organic phases are washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue is chromatographed on 250 g of silica gel
  8. extractionThe product, which is extracted with methylene chloride
  9. distillationis distilled in a bulb tube

Sources & evidence

ORD record
ord-c09c45fa428742069d21366548794733
Source dataset
uspto-grants-1980_11
Patent number
US04232039

Reaction notes

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