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

HRID 1073644Notes

Reaction equation

HRID 1073644 reaction equation
C(O)(=O)C.O.O1CCCC1.C1COCC1.[O:16]=[C:17]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1/[CH:31]=[CH:32]/[CH:33]=[CH:34]/[CH:35]([O:44]C1CCCCO1)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22]>C1COCC1>[OH:44][CH:35]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])/[CH:34]=[CH:33]/[CH:32]=[CH:31]/[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:17](=[O:16])[CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14582854methyl delta-oxo-2-[5-[(tetrahydro-2H-pyran-2-yl)oxyl]-1E,3E-tridecadienyl]benzenepentanoateHCID 22180045THF tetrahydrofurane

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1 ml 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 b 10 mg 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-0db8553fa8ee49129d4aca936b19c16f
Source dataset
uspto-grants-1990_11
Patent number
US04970234

Reaction notes

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