tert-Butanol → tert-Butyl ethyl malonate

HRID 1665652Notes

Reaction equation

HRID 1665652 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].[CH2:6]([O:8][C:9](=[O:14])[CH2:10][C:11](O)=[O:12])[CH3:7].C1CCC(N=C=NC2CCCCC2)CC1>C(#N)C>[CH2:6]([O:8][C:9](=[O:14])[CH2:10][C:11]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:12])[CH3:7]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 70615Monoethyl malonate

Product 1

HCID 96345tert-Butyl ethyl malonateYield 66.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

tert-butanol (2.8 mL, 37.8 mmol) was added to a stirred solution of malonic acid monoethyl ester (5 g, 37.8 mmol) in acetonitrile (45 mL). DCC (8.58 g, 41.6 mmol) dissolved in acetonitrile (5 mL) was added dropwise with stirring over a period of 2 hours. The reaction mixture was filtered and the filtrate was concentrated to afford 4.72 g (66%) of malonic acid tert-butyl ester ethyl ester. LCMS: 189.11 (M+1)+ 93.4%, 1H NMR: (CDCl3): δ 4.2 (q, 2H), 3.3 (s, 2H), 1.4 (s, 9H), 1.3 (t, 3H).

Workup

  1. additionwas added dropwise
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4c131494ac374d35a228ede3b739f3ef
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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