Methyl 7-bromoheptanoate → Methyl 5-oxocyclopent-1-ene-1-heptanoate

HRID 973103Notes

Reaction equation

HRID 973103 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][CH:6]=[CH:7][CH2:8][C:9]1[C:13](=[O:14])[CH2:12][CH2:11][CH:10]=1.[CH3:16][O:17][C:18](=[O:31])[CH2:19]CCC=CCC1C(=O)CCC=1.COC(=O)CCCCC=CCC1C(=O)CCC=1.BrCC=CCCC(OC)=O.BrCC=CCCCCC(OC)=O.BrCCCCCC(OC)=O.BrCCCCCCC(OC)=O.BrCCCCCCCC(OC)=O.BrCC#CCCCC(OC)=O>>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[C:13](=[O:14])[CH2:12][CH2:11][CH:10]=1.[CH3:16][O:17][C:18](=[O:31])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[C:13](=[O:14])[CH2:12][CH2:11][CH:10]=1.[CH3:16][O:17][C:18](=[O:31])[CH2:19][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[C:13](=[O:14])[CH2:12][CH2:11][CH:10]=1

Participants

12

Reactant 9

HCID 554086Methyl 7-bromoheptanoateHCID 4170292Methyl 6-BromohexanoateHCID 11107373Methyl 8-bromooctanoateHCID 11287432Methyl 7-bromohept-5-ynoateHCID 53917093Methyl 6-bromo-4-hexenoateHCID 54282459Methyl 6-(5-oxocyclopent-1-en-1-yl)hex-4-enoateHCID 544545348-(5-Oxocyclopent-1-enyl)-6-octenoic acid methyl esterHCID 54475740Methyl 8-bromo-6-octenoateHCID 54504603Methyl 7-(5-oxocyclopent-1-en-1-yl)hept-5-enoate

Product 3

HCID 2777884Methyl 5-oxocyclopent-1-ene-1-heptanoateHCID 14543894Methyl 8-(5-oxocyclopent-1-EN-1-YL)octanoateHCID 21420525Methyl 6-(5-oxo-1-cyclopenten-1-yl)hexanoate

Procedure

Alternatively 6-(5-oxocyclopent-1-enyl)-4-hexenoic acid methyl ester, 7-(5-oxocyclopent-1-enyl)-5-heptenoic acid methyl ester and 8-(5-oxocyclopent-1-enyl)-6-octenoic acid methyl ester, as well as, 6-(5-oxocyclopent-1enyl)hexanoic acid methyl ester, 7-(5-oxocyclopent-1-enyl)heptanoic acid methyl ester, and 8-(5-oxocyclopent-1-enyl)octanoic methyl ester are prepared by following serially the procedures of Examples 13, 14 and 15, and using methyl 6-bromo-4-hexenoate, methyl 7-bromo-5-heptanoate, methyl 8-bromo-6-octenoate, methyl 6-bromohexanoate, methyl 7-bromoheptanoate, and methyl 8-bromooctanoate, respectively, as starting material instead of methyl 7-bromo-5-heptynoate.

Sources & evidence

ORD record
ord-a973a92b0677429bb16dfecd0911b9ba
Source dataset
uspto-grants-1977_10
Patent number
US04054741

Reaction notes

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