Hydrochloric Acid → HCID 19088037, compound

HRID 1646799Notes

Reaction equation

HRID 1646799 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[CH3:12][C:13]1[C:18](=[O:19])[C:17]([CH3:20])=[C:16]([CH3:21])[C:15](=[O:22])[C:14]=1[CH:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32](OC)=[O:33].Cl>C(OCC)(=O)C.O>[CH3:12][C:13]1[C:18](=[O:19])[C:17]([CH3:20])=[C:16]([CH3:21])[C:15](=[O:22])[C:14]=1[CH:23]([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][OH:33]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 15229491HCID 15229491, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19088037HCID 19088037, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Lithium aluminum hydride (1.0 g, 27 mmole) was added to a tetrahydrofuran solution (50 ml) containing methyl 10-(3,5,6-trimethyl-1,4-benzoquinon -2-yl)-10-phenyldecanoate, (2.4 g, 6 mmole), followed by stirring for 3 hours with heating at 60° C. After the reaction solution was cooled, water was added to suspend the reaction, and 2N hydrochloric acid was added to adjust to pH 4.0. A 10% aqueous solution of ferric chloride (5 ml) was added to the mixture, and the reaction was allowed to proceed at room temperature for 10 minutes. Ethyl acetate was added to the reaction solution, and extraction was effected. The organic layer was washed with water, dried and concentrated under reduced pressure, and the residue was chromatographed on a silica gel column, followed by elution with isopropyl ether-ethyl acetate (1:1) to give 10-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-10-phenyldecan-1-ol (2.0 g). Its typical physical properties and nuclear magnetic resonance spectrum data are shown in Table 1. By following the procedure of this Example, the Compound Nos. 74 to 84 were prepared.

Workup

  1. temperatureAfter the reaction solution was cooled
  2. additionwas added
  3. waitto proceed at room temperature for 10 minutes
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was chromatographed on a silica gel column
  8. washfollowed by elution with isopropyl ether-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-8c775afc8f0d47389a633c65ed3c6269
Source dataset
uspto-grants-1993_01
Patent number
US05180742

Reaction notes

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