Allyl Alcohol → HCID 10058248, compound

HRID 358587Notes

Reaction equation

HRID 358587 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].[Li].[Na].[C:7]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:8][C:9]([CH3:11])=[O:10]>O1CCCC1>[CH2:14]([O:13][C:7](=[O:12])[CH2:8][C:9](=[O:10])[CH2:11][CH:1]([OH:4])[CH:2]=[CH2:3])[CH3:15]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 8868Ethyl AcetoacetateHCID 71354802Lithium, compd. with sodium (1:1)

Product 1

HCID 10058248HCID 10058248, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The allyl alcohol, 8, is reoxidized to the aldehyde, 9, by Swern oxidation, followed by an aldol condensation to the sodium lithium dianion of ethyl acetoacetate at -78° C. in tetrahydrofuran. (See Kraus, et al, J. Org. Chem., 48: 2111 (1983)) to form the 5-hydroxy-3-oxo-6-heptenoic acid-ethyl ester, 10.

Sources & evidence

ORD record
ord-4606522f14bc4fdc8456b43bb1dd8dc7
Source dataset
uspto-grants-1991_03
Patent number
US04997837

Reaction notes

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