Diketene → 5-(1-Hydroxy-3-oxobutylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 602430Notes

Reaction equation

HRID 602430 reaction equation
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.[CH2:11]=[C:12]1[O:16][C:14](=[O:15])[CH2:13]1>ClCCl>[OH:15][C:14](=[C:6]1[C:7](=[O:8])[O:9][C:2]([CH3:10])([CH3:1])[O:3][C:4]1=[O:5])[CH2:13][C:12](=[O:16])[CH3:11]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 547121045-(1-Hydroxy-3-oxobutylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above procedure is a modification of the procedure described in the literature at Kang, J; Kim, Y; Park, M; Lee, C.; Kim, W. Synthetic Communications (1984), 14(3), 265-9. In essence Meldrum's acid was reacted with diketene in dichloromethane in the presence of TEA at 20-25° C. for 2 hours to give 80% of 5-(1-hydroxy-3-oxobutylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (8).

Sources & evidence

ORD record
ord-84e19d9a7b55481aa85b7ddb3a560719
Source dataset
uspto-grants-2011_03
Patent number
US07906536B2

Reaction notes

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