Sodium hydride → HCID 54230691, compound

HRID 1579713Notes

Reaction equation

HRID 1579713 reaction equation
[CH3:1][C:2]1[C:7]([C:8](=O)[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:17][C:18]([OH:20])=[O:19].[H-].[Na+].[H][H].[C:25]([O:31][CH2:32]Cl)(=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27]>O>[CH3:1][C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:17][C:18]([O:20][CH2:32][O:31][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[O:19]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 87885Chloromethyl pivalateHCID 20455613HCID 20455613, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54230691HCID 54230691, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.37 g of the acid of Step A, 25 ml of hexamethylphosphortriamide and 0.57 g of a 50% suspension of sodium hydride in mineral oil stood until evolution of hydrogen ceased and then a solution of 1.78 g of chloromethyl pivalate in 10 ml of hexamethylphosphortriamide was progressively added thereto at room temperature. The mixture was stirred for 2 hours and was then poured into 250 ml of water. The mixture was extracted with isopropyl ether and the extracts were evaporated to dryness under reduced pressure. The residue was purified by chromatography over silica gel with a 95:5 mixture of methylene chloride-ethyl acetate as eluant. The fraction having Rf=0.65 was pivaloyloxymethyl 2-methyl-3-(p-chlorobenzoyl)-phenylacetate melting at 87°C.

Workup

  1. customat room temperature
  2. extractionThe mixture was extracted with isopropyl ether
  3. customthe extracts were evaporated to dryness under reduced pressure
  4. customThe residue was purified by chromatography over silica gel with a 95:5 mixture of methylene chloride-ethyl acetate as eluant

Sources & evidence

ORD record
ord-a1432b76f1ad427eba16462daa02871f
Source dataset
uspto-grants-1976_01
Patent number
US03931286

Reaction notes

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