HCID 12594356, compound → HCID 21437425, compound

HRID 2397256Notes

Reaction equation

HRID 2397256 reaction equation
O1C=CC=C1CCC[C:9]([O:11][CH:12](C)C)=[O:10].[CH2:15]([O:18][C:19]1([CH2:28][CH2:29][CH2:30][C:31](OC(C)C)=O)[CH:23]=[CH:22][CH:21]([O:24][CH2:25][CH2:26]C)[O:20]1)[CH2:16]C.O1C=CC=C1CCCCC(OC)=O>[PH4+].C(O)CC.C(O)C>[CH2:15]([O:18][C:19]1([CH2:28][CH2:29][CH2:30][CH2:31][C:9]([O:11][CH3:12])=[O:10])[CH:23]=[CH:22][CH:21]([O:24][CH2:25][CH3:26])[O:20]1)[CH3:16]

Participants

7

Reactant 3

HCID 12594356HCID 12594356, compoundHCID 21437419HCID 21437419, compoundHCID 21437427HCID 21437427, compound

Product 1

HCID 21437425HCID 21437425, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 10311-PropanolSolventHCID 5460504PhosphoniumSolvent

Procedure

Adaptation of the above-described procedures to the preparation of the other compounds of this invention essentially involves the lengthening or shortening of, or the introduction of one or two lower alkyl groups into, the side-chains in furans (I) or (XVII) or in phosphonium derivative (III). These adaptations can be accomplished by procedures well-known to the art. For example, isopropyl γ-(2-furyl)-butyrate provides 2,5-dihydro-2,5-di-n-propoxy-2-(3'-carboisopropoxypropyl)furan in n-propanol whereas methyl δ-(2-furyl)valerate provides 2,5-dihydro-2,5-diethoxy-2-(4'-carbomethoxybutyl)furan in ethanol when treated in the manner described for the conversion of (I) to (II). Similarly, ω-(2-furyl)caproic acid and ω-(2-furyl)enanthic acid provide 2,5-dihydro-2,5-diethoxy-2-(5'-carboxyentyl)furan and 2,5-dihydro-2,5-diethoxy-2-(6'-carboxyhexyl)furan when treated in ethanol in the manner described for the conversion of (XVII) to (XVIII). Optionally, the furyl acids may be first esterified prior to oxidative alkoxylation, and all 2,5-dihydro-2,5-dialkoxy-2-(carboalkoxyalkyl)furans may be converted to the corresponding aldehydes in the manner described for the conversion of (II) to (IV). Also, the reaction of 3-carboxypropyltriphenylphosphonium bromide and 5-carboxy-3,4-dimethylamyltriphenylphosphonium bromide with 2,5-dihydro-2,5-diethoxy-2-(4'-oxobutyl)furan and 2,5-dihydro-2,5-diethoxy-2-(2'-oxoethyl)furan, respectively, provides the 2,5-dihydro-2,5-diethoxy-2-(7'-carboxy-4'-cis-heptenyl)furan and 2,5-dihydro-2,5-diethoxy-2-(7'-carboxy-5',6'-dimethyl-2-cis-heptenyl)furan.

Workup

  1. customAdaptation of the above-described procedures to the preparation of the other compounds of this invention

Sources & evidence

ORD record
ord-1f6c146c752b4562b6817db107bd8c42
Source dataset
uspto-grants-1977_05
Patent number
US04021452

Reaction notes

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