Isopropyl 4-chloroacetoacetate → HCID 20477515, compound

HRID 905114Notes

Reaction equation

HRID 905114 reaction equation
[Na].C(OC(=O)CC(CCl)=O)(C)C.[CH:13]([O:16][C:17](=[O:30])[CH2:18][C:19]([CH2:21][O:22]CC1C=CC=CC=1)=[O:20])([CH3:15])[CH3:14]>O1CCCC1>[CH:13]([O:16][C:17](=[O:30])[CH2:18][C:19]([CH2:21][OH:22])=[O:20])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 2795580Isopropyl 4-chloroacetoacetateHCID 5360545SodiumHCID 18172563HCID 18172563, compound

Product 1

HCID 20477515HCID 20477515, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium benzylate in tetrahydrofuran was reacted using the procedure of Example 1 with 4-chloroacetoacetic isopropyl ester. The resultant 4-benzyloxyacetoacetic acid isopropyl ester was subsequently hydrogenolyzed. The 4-hydroxyacetoacetic isopropyl ester thus formed was converted at ambient temperature into tetronic acid by treatment with 18 percent HCl. The total yield, related to the 4-chloroacetoacetic isopropyl ester, was 78 percent.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-1201c4f1ae8e4db49c9bf95fe0749287
Source dataset
uspto-grants-1983_12
Patent number
US04421922

Reaction notes

Loading…