3-Hydroxy-4H-pyran-4-one → 2,2-Dimethyl-3-(3-propoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid

HRID 1762598Notes

Reaction equation

HRID 1762598 reaction equation
[CH3:1][C:2]1([CH3:16])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH2:10][CH2:11][CH3:12])=[O:8])[CH:3]1[C:13]([OH:15])=[O:14].O=C1C=COC=C1O>>[CH3:16][C:2]1([CH3:1])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH2:10][CH2:11][CH3:12])=[O:8])[CH:3]1[C:13]([OH:15])=[O:14].[CH3:1][C:2]1([CH3:16])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH3:10])=[O:8])[CH:3]1[C:13]([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 681293-Hydroxy-4H-pyran-4-oneHCID 545705842,2-Dimethyl-3-(3-propoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid

Product 2

HCID 545705842,2-Dimethyl-3-(3-propoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acidHCID 867430702,2-Dimethyl-3-(3-methoxy-3-oxo-1-propeny)-cyclopropane-carboxylate

Procedure

Using the procedure of Example 9, (1R, cis, ΔZ) 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid and 4-oxo-(4H)-pyran-3-yl alcohol were reacted to obtain 4-oxo-4(H)-pyran-3-yl (1R, cis, ΔZ) 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl)-cyclopropane-carboxylate melting at 106° C. and having a specific rotation of [α]D20 =+153°±2.5° (c=0.8% in benzene).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-f03f030cb3a24d3a8bef36c37b17e452
Source dataset
uspto-grants-1989_05
Patent number
US04833163

Reaction notes

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