Pyridine → 1-(2,3-Dihydrobenzofuran-5-yl)propan-2-one

HRID 429813Notes

Reaction equation

HRID 429813 reaction equation
[CH3:1][C:2](=C)[CH2:3][C:4]1[CH:5]=[CH:6][C:7]2[O:11][CH2:10][CH2:9][C:8]=2[CH:12]=1.N1C=CC=CC=1.[O:20]=[O+][O-].NC(N)=S>C(Cl)Cl.CO>[O:11]1[C:7]2[CH:6]=[CH:5][C:4]([CH2:3][C:2](=[O:20])[CH3:1])=[CH:12][C:8]=2[CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 24823OzoneHCID 2723790ThioureaHCID 183528785-(2-Methylallyl)-2,3-dihydrobenzofuran

Product 1

HCID 183527681-(2,3-Dihydrobenzofuran-5-yl)propan-2-oneYield 54%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(2-methylallyl)-2,3-dihydrobenzofuran (58 grams, 0.333 mole) and pyridine (27 ml) in methylene chloride (450 ml) and methanol (150 ml) was cooled in a dry ice/acetone bath and a stream of ozone passed through for 1.0 hour. Thiourea (18 grams, 0.24 mole) was added and the mixture was warmed to room temperature. The resultant precipitate was filtered and the mother liquor evaporated to give an oil which was distilled under reduced pressure to give 1-(2,3-dihydrobenzofuran-5-yl)propan-2-one (32 grams, 54%), bp. 110° C. @ 120 mT.

Workup

  1. custompassed through for 1.0 hour
  2. filtrationThe resultant precipitate was filtered
  3. customthe mother liquor evaporated
  4. customto give an oil which
  5. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-bd0ba028d81047af97497267bc46110a
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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