Methanol → HCID 54271104, compound

HRID 1637110Notes

Reaction equation

HRID 1637110 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][OH:31]>>[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:31][CH3:30])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 53716900HCID 53716900, compound

Product 1

HCID 54271104HCID 54271104, compoundYield 4%

Procedure

(+/-)-1 -Phenyl-3-(3-cyclopentyloxy-4-methoxyphenyl)-5-oxo-6-diazohexyne (120 mg, 0.35 mmol) was added portionwise to a refluxing solution of BF3 ·Et2O (0.5 ml) in MeOH (20 ml). After 5 min, the solvent was concentrated, the reaction diluted with H2O, basified with NaHCO3, and extracted with Et2O. The extracts were washed with H2O, dried, and the solvent removed. Purification by flash chromatography (silica gel, 30% Et2O in hexane) gave the titled product (4.8 mg, 4%). 1H NMR (400 MHz, CDCl3) δ 7.42 (m, 2 H), 7.30 (m, 3 H), 6.98 (m, 2 H), 6.84 (d, 1 H), 4.80 (m, 1 H), 4.40 (t, 1 H), 4.06 (d, 1 H), 3.92 (d, 1 H), 3.84 (s, 3 H), 3.38 (s, 3 H), 3.04 (d of d, 1 H), 2.88 (d of d, 1 H), 1.68-2.00 (m, 6 H), 1.58 (m, 2 H).

Workup

  1. concentrationthe solvent was concentrated
  2. additionthe reaction diluted with H2O
  3. extractionextracted with Et2O
  4. washThe extracts were washed with H2O
  5. customdried
  6. customthe solvent removed
  7. customPurification by flash chromatography (silica gel, 30% Et2O in hexane)

Sources & evidence

ORD record
ord-7d6b9f918eb84580adbbe4a986251e77
Source dataset
uspto-grants-2000_03
Patent number
US06037367

Reaction notes

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