Acetyl chloride → HCID 85826160, compound

HRID 2064673Notes

Reaction equation

HRID 2064673 reaction equation
[Cl-].[Mg+2].[Cl-].[CH2:4]([O:6][C:7](=[O:17])[CH2:8][C:9](=[O:16])[CH2:10][O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH3:5].[C:18](Cl)(=[O:20])[CH3:19].[Cl-].[NH4+]>ClCCl.N1C=CC=CC=1>[CH2:4]([O:6][C:7](=[O:17])[CH:8]([C:18](=[O:20])[CH3:19])[C:9](=[O:16])[CH2:10][O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[CH3:5]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 25517Ammonium ChlorideHCID 5360315Magnesium ChlorideHCID 11790264Ethyl 4-t-butoxyacetoacetate

Product 1

HCID 85826160HCID 85826160, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of dry magnesium chloride (0.471 g) in dichloromethane (6 ml) was treated with 4-tert-butoxy-3-oxo-butyric acid ethyl ester [1.00 g, Reference Example 43]. This mixture was cooled to 0° C., then treated with pyridine (0.80 ml), then stirred for 15 minutes at 0° C. and then treated with acetyl chloride (0.352 ml). After stirring for a further 15 minutes at 0° C. and then for 1 hour at ambient temperature the reaction mixture was treated with saturated aqueous ammonium chloride solution and then extracted twice with ethyl acetate. The combined extracts were dried over magnesium sulfate and then evaporated to yield 2-acetyl-4-tert-butoxy-3-oxo-butyric acid ethyl ester (1.15 g) as a yellow oil which was used without further purification. LC-MS (METHOD B): RT=3.16 minutes; 243 (M−H)−.

Workup

  1. stirringAfter stirring for a further 15 minutes at 0° C.
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-911552e7b9464f0991adb0a205215e01
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

Loading…