Hydrochloric Acid → HCID 15230864, compound

HRID 1464503Notes

Reaction equation

HRID 1464503 reaction equation
Cl.[CH3:2][C:3]1[C:8](=[O:9])[C:7]([CH3:10])=[C:6]([CH3:11])[C:5](=[O:12])[C:4]=1[CH:13]([C:23]1[S:24][CH:25]=[CH:26][CH:27]=1)[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20]CC)=[O:19].C(OC(C)C)(C)C>O1CCCC1>[CH3:2][C:3]1[C:8](=[O:9])[C:7]([CH3:10])=[C:6]([CH3:11])[C:5](=[O:12])[C:4]=1[CH:13]([C:23]1[S:24][CH:25]=[CH:26][CH:27]=1)[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 15229489HCID 15229489, compound

Product 1

HCID 15230864HCID 15230864, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

6N Hydrochloric acid (10 ml) was added to a solution of ethyl 6-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-6-(2-thienyl)hexanoate (1.7 g, 4.5 mmole) in tetrahydrofuran (10 ml), followed by stirring for 17 hours with heating at 70° C. After cooling, isopropyl ether was added to the mixture, and the organic layer was washed twice with water, dried and concentrated under reduced pressure. The residue was chromatographed on a silica gel column, and elution was performed with isopropyl ether-ethyl acetate (1:1), followed by recrystallization from isopropyl ether to give 6-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-6-(2-thienyl)hexanoic acid (1.1 g, 70%).

Workup

  1. temperatureAfter cooling
  2. washthe organic layer was washed twice with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on a silica gel column, and elution
  6. customfollowed by recrystallization from isopropyl ether

Sources & evidence

ORD record
ord-50afce3ae1b746d1a46b6363f97603c5
Source dataset
uspto-grants-1994_04
Patent number
US05304658

Reaction notes

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