(3-Carboxypropyl)(triphenyl)phosphanium bromide → HCID 86733260, compound

HRID 2397257Notes

Reaction equation

HRID 2397257 reaction equation
[Br-].C(CCC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(O)=O.[Br-].[C:28]([CH2:31][CH:32]([CH3:56])[CH:33]([CH3:55])[CH2:34][CH2:35][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:30])=[O:29].[CH2:57]([O:59][C:60]1([CH2:68][CH2:69]CC=O)[CH:64]=[CH:63][CH:62]([O:65][CH2:66][CH3:67])[O:61]1)[CH3:58].C(OC1(CC=O)C=CC(OCC)O1)C>C(O)C>[CH2:57]([O:59][C:60]1(/[CH:68]=[CH:69]\[CH2:35][CH2:34][CH:33]([CH3:55])[CH:32]([CH3:56])[CH2:31][C:28]([OH:30])=[O:29])[CH:64]=[CH:63][CH:62]([O:65][CH2:66][CH3:67])[O:61]1)[CH3:58]

Participants

6

Reactant 4

HCID 10717451(3-Carboxypropyl)(triphenyl)phosphanium bromideHCID 214374262,5-Dihydro-2,5-diethoxy-2-(2'-oxoethyl)furanHCID 214374312,5-Dihydro-2,5-diethoxy-2-(4'-oxobutyl)furanHCID 86733261HCID 86733261, compound

Product 1

HCID 86733260HCID 86733260, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Sources & evidence

ORD record
ord-1181956c3e7144c193012befb4595a69
Source dataset
uspto-grants-1977_05
Patent number
US04021452

Reaction notes

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