Acetic Acid → methyl 2-(5-hydroxy-1E,3E,-tridecandienyl)-delta-oxobenzenpentanoate

HRID 1722340Notes

Reaction equation

HRID 1722340 reaction equation
C(O)(=O)C.O.[O:6]=[C:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1/[CH:21]=[CH:22]/[CH:23]=[CH:24]/[CH:25]([O:34]C1CCCCO1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12]>O1CCCC1>[OH:34][CH:25]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])/[CH:24]=[CH:23]/[CH:22]=[CH:21]/[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:7](=[O:6])[CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 14582854methyl delta-oxo-2-[5-[(tetrahydro-2H-pyran-2-yl)oxyl]-1E,3E-tridecadienyl]benzenepentanoate

Product 1

HCID 14798470methyl 2-(5-hydroxy-1E,3E,-tridecandienyl)-delta-oxobenzenpentanoateYield 60.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 1ml of a 3:1:1 solution of acetic acid, water, and tetrahydrofuran (THF) was added 20mg (0.041 mmol) of the titled product of Example 10 and the reaction mixture was allowed to stir 16 hr. After this time, some insoluble oil was still present and approximately 50μl of THF was added to the reaction mixture and it was stirred for an additional 2 hours. The volatile components were removed in vacuo and the residue was flash chromatographed. Elution with 1:1 diethylether-hexane produced 10mg of the desired product.

Workup

  1. stirringwas stirred for an additional 2 hours
  2. customThe volatile components were removed in vacuo
  3. customchromatographed
  4. washElution with 1:1 diethylether-hexane

Sources & evidence

ORD record
ord-ce5c83b9f7f24f73b4ea82e131cf17dc
Source dataset
uspto-grants-1989_08
Patent number
US04855324

Reaction notes

Loading…