6-Carbomethoxymethyl-6-ethyl-2-cyclohexen-1-one → 1-Ethyl-2-hydroxy-3-cyclohexeneethanol

HRID 231648Notes

Reaction equation

HRID 231648 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1([CH2:12][CH3:13])[CH2:10][CH2:9][CH:8]=[CH:7][C:6]1=[O:11].[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH2:12]([C:5]1([CH2:4][CH2:3][OH:2])[CH2:10][CH2:9][CH:8]=[CH:7][CH:6]1[OH:11])[CH3:13]

Participants

4

Reactant 2

HCID 136492416-Carbomethoxymethyl-6-ethyl-2-cyclohexen-1-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 142814701-Ethyl-2-hydroxy-3-cyclohexeneethanolYield 103%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1-ethyl-2-oxocyclohex-3-eneacetic acid methyl ester (5.00 g, 25.48 mmol) in 10 mL of anhydrous ether was added dropwise under nitrogen to a 0° C. solution of lithium aluminum hydride (967 mg, 25.48 mmol) in 25 mL of anhydrous ether. The reaction was quenched by dropwise addition of 0.97 mL of water, 0.97 mL of 1M NaOH (aqueous) and 2.7 mL of water. The solution was filtered and the salts were boiled 3× in 25 mL of ethyl acetate and these washings were combined with the first filtrate. The filtrate was concentrated in vacuo to afford 4.47 g (103%) of product as a colorless oil.

Workup

  1. customThe reaction was quenched by dropwise addition of 0.97 mL of water, 0.97 mL of 1M NaOH (aqueous) and 2.7 mL of water
  2. filtrationThe solution was filtered
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d8424c24824b4d7cb047ee59505717b3
Source dataset
uspto-grants-1989_07
Patent number
US04847389

Reaction notes

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