N,N,N',N'-Tetramethylethylenediamine → Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

HRID 1197325Notes

Reaction equation

HRID 1197325 reaction equation
CN(C)CCN(C)C.[CH3:9][O:10][C:11]([CH:13]1[CH2:18][CH2:17][CH:16]([C:19](Cl)=[O:20])[CH2:15][CH2:14]1)=[O:12]>C1COCC1.[BH4-].[Zn+2].[BH4-]>[OH:20][CH2:19][CH:16]1[CH2:15][CH2:14][CH:13]([C:11]([O:10][CH3:9])=[O:12])[CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 15380636Methyl 4-(chlorocarbonyl)cyclohexane-1-carboxylate

Product 1

HCID 11073869Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

Reagents, catalysts & solvents 2

HCID 12838295ZINC;boranuideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Zinc borohydride solution (67 ml of a 0.35M solution, Ref. W. J. Gensler et al J Amer. Chem. Soc. 1960, 82, 6074) and tetramethylethylendiamine (TMEDA) were successively added to a stirred solution of 4-methoxycarbonylcyclohexylcarbonyl chloride (1.02 g) in THF (18 ml) at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes. The organic phase was then washed with dilute hydrochloric acid and brine before drying over anhydrous magnesium sulphate and then evaporation in vacuo. Methyl 4-hydroxymethylcyclohexanecarboxylate was obtained as a semi-crystalline oil.

Workup

  1. washThe organic phase was then washed with dilute hydrochloric acid and brine
  2. dry with materialbefore drying over anhydrous magnesium sulphate
  3. customevaporation in vacuo

Sources & evidence

ORD record
ord-e83e6e928ea5409eb06ce5ce0cbd8223
Source dataset
uspto-grants-1992_05
Patent number
US05116862

Reaction notes

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