Sodium hydride → Ethyl Acetoacetate

HRID 2351365Notes

Reaction equation

HRID 2351365 reaction equation
[N+:1](C1C=C(C=O)C(O)=CC=1)([O-])=[O:2].[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C([O:26][C:27]([CH2:29]CCOC1C=CC([N+]([O-])=O)=CC=1C=O)=[O:28])C>N1C=CC=CC=1.CN(C)C=O>[C:19]([O:21][CH2:22][CH3:23])(=[O:20])[CH2:18][C:17]([CH3:16])=[O:2].[C:27]([O-:28])(=[O:26])[CH3:29].[NH4+:1]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 668085-NitrosalicylaldehydeHCID 76300Ethyl 4-bromobutyrateHCID 19846252HCID 19846252, compound

Product 2

HCID 8868Ethyl AcetoacetateHCID 517165Ammonium Acetate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

The last two compounds in the second table above were intermediates for the fourth compound in the first table above, and were prepared by initial reaction of 5-nitrosalicylaldehyde (16.7 g.), sodium hydride (2.64 g. of a 50% dispersion in oil), ethyl 4-bromobutyrate (15.74 g.) and dimethylformamide (200 ml.) at 100° C. for 4 hours, and then reaction of the 2-(3-ethoxycarbonylpropoxy)-5-nitrobenzaldehyde (m.p. 61°-62° C.) thus obtained (1.5 g.), ethyl acetoacetate (1.0 ml.), ammonium acetate (0.36 g.) and pyridine (25 ml.) at 100° C. for 5 hours.

Workup

  1. customwere prepared by initial

Sources & evidence

ORD record
ord-e396d4ecc3214c17a7164ddf7aeebde1
Source dataset
uspto-grants-1989_10
Patent number
US04873254

Reaction notes

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