Octanoic Acid → HCID 14251021, compound

HRID 1722059Notes

Reaction equation

HRID 1722059 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([CH:21]1[CH2:31][C:24]2[S:25][C:26]([C:28]([OH:30])=[O:29])=[CH:27][C:23]=2[CH2:22]1)[CH2:17][CH2:18][CH2:19][CH3:20].BrCC1C=CSC=1.C(C(O)=O)CCCCCC.C([N-]C(C)C)(C)C.[Li+].[CH2:57]([C:64]1[CH:69]=[CH:68][C:67](O)=[CH:66][CH:65]=1)[CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:16]([CH:21]1[CH2:31][C:24]2[S:25][C:26]([C:28]([O:30][C:67]3[CH:66]=[CH:65][C:64]([CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])=[CH:69][CH:68]=3)=[O:29])=[CH:27][C:23]=2[CH2:22]1)[CH2:17][CH2:18][CH2:19][CH3:20]

Participants

9

Reactant 6

HCID 379Octanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 161434-HeptylphenolHCID 5207033-(Bromomethyl)thiopheneHCID 2724682Lithium diisopropylamideHCID 14251020HCID 14251020, compound

Product 1

HCID 14251021HCID 14251021, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

1.63 g of dicyclohexylcarbodiimide in 2.5 ml of methylene chloride are added to a mixture of 1.78 g of 5-n-pentyl-5,6-dihydro-4-H-cyclopenta[b]thiophene-2-carboxylic acid (which can be prepared from 3-bromomethylthiophene by reaction with n-heptanecarboxylic acid and lithium diisopropylamide, subsequent cyclization via the corresponding acid chloride, reduction of the carbonyl group (for example Wolff-Kishner reduction), Friedel-Crafts acetylation and a haloform reaction), 0.098 g of 4-dimethylaminopyridine, 1.42 g of 4-n-heptylphenol and 12 ml of methylene chloride at 10°, with stirring. After the mixture has been stirred at room temperature for 15 hours, it is filtered with suction over silica gel and the solvent is evaporated off. Recrystallization from ethanol gives 4-n-heptylphenyl 5-n-pentyl-5,6-dihydro-4-H-cyclopenta[b]thiophene-2-carboxylate of m.p. 64° and c.p. 82°.

Workup

  1. stirringAfter the mixture has been stirred at room temperature for 15 hours
  2. filtrationit is filtered with suction over silica gel
  3. customthe solvent is evaporated off
  4. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-618f2e267a9d40618c47d0d014d47921
Source dataset
uspto-grants-1989_08
Patent number
US04853149

Reaction notes

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