HCID 13251304, compound → Isoxepac

HRID 1649492Notes

Reaction equation

HRID 1649492 reaction equation
Cl[CH:2]([C:6]1[CH:21]=[CH:20][C:9]2[O:10][CH2:11][C:12]3[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=3[C:14](=[O:15])[C:8]=2[CH:7]=1)[C:3]([OH:5])=[O:4].[H][H]>[C].[Pd].C(OCC)(=O)C>[O:15]=[C:14]1[C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[CH2:11][O:10][C:9]2[CH:20]=[CH:21][C:6]([CH2:2][C:3]([OH:5])=[O:4])=[CH:7][C:8]1=2

Participants

5

Reactant 2

HCID 13251304HCID 13251304, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 41448Isoxepac

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture containing 6,11-dihydro-α-chloro-11-oxodibenz[b,e]oxepin-2-acetic acid in the amount of 0.2 grams, 0.2 grams of 5% palladium-carbon reduction catalyst, 30 ml ethyl acetate and commercially available 4Å molecular sieve (Davidson Grade 514, Type 4A, 8-12 mesh beads, alumina silicate base with sodium cation, available from W. R. Grace) was treated with hydrogen (10 psi). The reduction reaction was run for 4 hours and then worked up by filtration and concentration in vacuo to yield 0.18 grams of crude product. 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetic acid (V) was obtained after purification by chromatography on silica gel using ethyl acetate. Its structure was confirmed by comparison of its infra-red, proton-NMR and thin layer chromatography with that of an authentic sample.

Workup

  1. customThe reduction reaction
  2. filtrationworked up by filtration and concentration in vacuo
  3. customto yield 0.18 grams of crude product

Sources & evidence

ORD record
ord-228c03f0709f40fb9820f2f1800a6af7
Source dataset
uspto-grants-1983_11
Patent number
US04417063

Reaction notes

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