Hydrochloric Acid → HCID 13745946, compound

HRID 2290670Notes

Reaction equation

HRID 2290670 reaction equation
[C:1]([C:4]1[CH:17]=[CH:16][C:7]2[O:8][CH2:9][CH:10](S(C)(=O)=O)[CH2:11][C:6]=2[C:5]=1[OH:18])(=[O:3])[CH3:2].[OH:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:22][C:21]=1[CH2:31][CH2:32][CH3:33].[H-].[Na+].C1OCCOCCOCCOCCOC1.[H][H].Cl>C1(C)C=CC=CC=1>[C:1]([C:4]1[CH:17]=[CH:16][C:7]2[O:8][CH2:9][CH:10]([O:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:22][C:21]=3[CH2:31][CH2:32][CH3:33])[CH2:11][C:6]=2[C:5]=1[OH:18])(=[O:3])[CH3:2]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 20231630HCID 20231630, compoundHCID 22459111HCID 22459111, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13745946HCID 13745946, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The compound of Example 9 (1.13 g), methyl 4-hydroxy-3-propylphenylacetate (800 mg) and sodium hydride (59%, 320 mg) in dry toluene (50 ml) were stirred at room temperature under nitrogen for 30 minutes in an ultrasonic bath. 15-Crown-5 (about 1.5 ml) was added slowly until hydrogen evolution ceased. The reaction mixture was then heated at 110° for 15 minutes. The reaction was cooled to room temperature and poured into a mixture of ice and 1N HCl. The ice mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried and concentrated in vacuo. The residue was purified by chromatography on silica gel to afford the title compound, m.p. 59°-60°.

Workup

  1. temperatureThe reaction mixture was then heated at 110° for 15 minutes
  2. extractionThe ice mixture was extracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e7cbee891f7842289f8ff5cbb7d3cb53
Source dataset
uspto-grants-1986_10
Patent number
US04617407

Reaction notes

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