Water → Lithium tert-butoxycarbonyl-acetate

HRID 1665653Notes

Reaction equation

HRID 1665653 reaction equation
O[Li:2].O.C([O:6][C:7](=[O:16])[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])C.C1COCC1.O>CO>[C:12]([O:11][C:9]([CH2:8][C:7]([O-:16])=[O:6])=[O:10])([CH3:15])([CH3:13])[CH3:14].[Li+:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 96345tert-Butyl ethyl malonateHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 86634609Lithium tert-butoxycarbonyl-acetateYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

LiOH.H2O (1.57 g, 37 mmol) was added to a solution of malonic acid tert-butyl ester ethyl ester (4.7 g, 25 mmol) in a mixture of methanol (23 mL), THF (47 mL) and H2O (14 mL). The reaction mixture was stirred for 1 hour at room temperature then concentrated to afford 4.0 g (96%) of lithium tert-butoxycarbonyl-acetate. 1H NMR: (DMSO-d6): δ 2.8 (s, 2H), 1.4 (s, 9H).

Workup

  1. concentrationthen concentrated

Sources & evidence

ORD record
ord-933283191230445e9cdc4c7ddf1ed0c6
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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