Acetic Acid → HCID 54564316, compound

HRID 1637108Notes

Reaction equation

HRID 1637108 reaction equation
[C:1]1([C:7]#[C:8][CH:9]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:17]=2)[CH2:10][C:11](=[O:15])[CH:12]=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:30][C:31]([OH:33])=[O:32]>O>[C:1]1([C:7]#[C:8][CH:9]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:17]=2)[CH2:10][C:11](=[O:15])[CH2:12][O:33][C:31](=[O:32])[CH3:30])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 53716900HCID 53716900, compound

Product 1

HCID 54564316HCID 54564316, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of (+/-)-1-phenyl-3-(3-cyclopentyloxy-4-methoxyphenyl)-5-oxo-6-diazohexyne (190 mg, 0.55 mmol) in HOAc (1 ml) was heated to 70° for 30 min. The reaction was cooled, diluted with H2O, and extracted with CHCl3. The extracts were washed with H2O, 5% NaHCO3, dried, and the solvent evaporated. Purification by flash chromatography (silica gel, 50% Et2O in hexane) gave the titled compound as an oil (132 mg, 63%). 1H NMR (400 MHz, CDCl3 ) δ 7.42 (m, 2 H), 7.30 (m, 3 H), 6.96 (m, 2 H), 6.82 (d, 1 H), 4.80 (m, 1 H), 4.72 (d, 1 H), 4.56 (d, 1 H), 4.36 (t, 1 H), 3.86 (s, 3 H), 3.04 (d of d, 1 H), 2.85 (d of d, 1 H), 2.16 (s, 3 H), 1.72-2.00 (m, 6 H), 1.54-1.64 (m, 2 H).

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with CHCl3
  3. washThe extracts were washed with H2O, 5% NaHCO3
  4. customdried
  5. customthe solvent evaporated
  6. customPurification by flash chromatography (silica gel, 50% Et2O in hexane)

Sources & evidence

ORD record
ord-bb9db76be6c54b7b87d99102847e08d2
Source dataset
uspto-grants-2000_03
Patent number
US06037367

Reaction notes

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