Pyridine → HCID 19425522, compound

HRID 742364Notes

Reaction equation

HRID 742364 reaction equation
[Si:1]([O:8][C:9]1[C:17]([CH2:18]/[CH:19]=C(\C)/CCC(OC)=O)=[C:16]([CH2:28][CH3:29])[C:15]([CH3:30])=[C:14]2[C:10]=1[C:11](=[O:31])[O:12][CH2:13]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CC=CC=1.[O:38]=[O+][O-]>C(Cl)Cl.CO>[Si:1]([O:8][C:9]1[C:17]([CH2:18][CH:19]=[O:38])=[C:16]([CH2:28][CH3:29])[C:15]([CH3:30])=[C:14]2[C:10]=1[C:11](=[O:31])[O:12][CH2:13]2)([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 24823OzoneHCID 131719101HCID 131719101, compound

Product 1

HCID 19425522HCID 19425522, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of methyl (E)-6-(4-t-butyldimethylsilyloxy-1,3-dihydro-6- ethyl-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate (10.6 g) in methylene chloride (150 ml), methanol (150 ml), and pyridine (5 ml) was treated with an excess of ozone at -70° C. The reaction was quenched with dimethylsulfide (20 ml) and stirred for 5 hours at 25° C. The reaction mixture was poured into 1N aqueous sodium hydrogen mullets. Extraction with 1:1 ethyl acetate:hexane gave an oil which on purification by silica gel chromatography gave 2-(4-t-butyldimethylsilyloxy-1,3-dihydro-6-ethyl-7-methyl-3-oxoisobenzofuran-5-yl)-acetaldehyde, m.p. 90.9°-91.6° C.

Workup

  1. customThe reaction was quenched with dimethylsulfide (20 ml)
  2. additionThe reaction mixture was poured into 1N aqueous sodium hydrogen mullets
  3. extractionExtraction with 1:1 ethyl acetate
  4. customhexane gave an oil which
  5. customon purification by silica gel chromatography

Sources & evidence

ORD record
ord-166a6a447d094910988a63baaf7a44f0
Source dataset
uspto-grants-1996_09
Patent number
US05554612

Reaction notes

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