tert-Butyl 4-chloro-3-oxobutyrate → HCID 178451313, compound

HRID 1032850Notes

Reaction equation

HRID 1032850 reaction equation
[N:1]([O-:3])=O.[Na+].[Cl:5][CH2:6][C:7](=[O:16])[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]>O.C(O)(=O)C.C(=O)(O)[O-].[Na+].[Cl-].[Na+].O>[Cl:5][CH2:6][C:7](=[O:16])/[C:8](=[N:1]/[OH:3])/[C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10]

Participants

7

Reactant 2

HCID 2724514tert-Butyl 4-chloro-3-oxobutyrateHCID 23668193Sodium Nitrite

Product 1

HCID 178451313HCID 178451313, compoundYield 91%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolvent4×HCID 516892Sodium BicarbonateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 35.6 g of sodium nitrite in 100 ml of water was added to a cold solution of t-butyl 4-chloro-3-oxobutanoate (100.9 g, 0.439 moles of 84% material*) in 400 ml of acetic acid containing 50 ml of water over a 0.5 hour period with stirring. The mixture was stirred in the cold for an additional hour, then stored in the cold overnight. The mixture was diluted with 500 ml portions of water, 500 ml of saturated sodium bicarbonate, 500 ml of water and 500 ml of brine, then dried over magnesium sulfate and evaporated to give an amber oil; yield 88.6 g (91% yield). This material was used in the next step without further purification. *This compound was obtained from Lonza Chemical Co., Fair Lawn, N.J.

Workup

  1. stirringThe mixture was stirred in the cold for an additional hour
  2. customstored in the cold overnight
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto give an amber oil
  6. customThis material was used in the next step without further purification

Sources & evidence

ORD record
ord-4742012821f842acac365f48f73492d1
Source dataset
uspto-grants-1990_09
Patent number
US04959495

Reaction notes

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