Tetrahydrofuran → HCID 18707320, compound

HRID 1421991Notes

Reaction equation

HRID 1421991 reaction equation
[CH3:1][C:2](C)([O-:4])C.[K+].[CH2:7]([O:9][C:10]1[CH:11]=[C:12]([C:19]2[S:20][CH:21]=[C:22]([C:24]3[CH:29]=[C:28]([CH:30]=[O:31])[C:27]([O:32][CH2:33][O:34][CH3:35])=[C:26]([C:36]([O:38][CH3:39])=[O:37])[CH:25]=3)[N:23]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH3:18])[CH3:8].[O:40]1CCC[CH2:41]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:7]([O:9][C:10]1[CH:11]=[C:12]([C:19]2[S:20][CH:21]=[C:22]([C:24]3[CH:29]=[C:28]([CH:30]=[O:31])[C:27]([O:32][CH2:33][O:34][CH3:35])=[C:26]([C:36]([O:38][CH2:39][O:4][CH3:2])=[O:37])[CH:25]=3)[N:23]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH3:18])[CH3:8].[CH2:7]([O:9][C:10]1[CH:11]=[C:12]([C:19]2[S:20][CH:21]=[C:22]([C:24]3[CH:29]=[C:28]([CH:30]([OH:31])[CH:2]([OH:4])[CH3:1])[C:27]([O:32][CH2:33][O:34][CH3:35])=[C:26]([C:36]([O:38][CH2:39][O:40][CH3:41])=[O:37])[CH:25]=3)[N:23]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH3:18])[CH3:8]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 18707338HCID 18707338, compoundHCID 23665647Potassium tert-butoxide

Product 2

HCID 18707320HCID 18707320, compoundHCID 53716240HCID 53716240, compound

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

535 mg of methyltriphenylphosphonium bromide was suspended in 10 ml of tetrahydrofuran with stirring. Thereto was added 190 mg of potassium tert-butoxide at -5° C., and the mixture was stirred at the same temperature for 1 hour. Thereto was added 500 mg of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-methoxymethoxy-5-formylphenyl)thiazole. The mixture was stirred at the same temperature for 2 hours and at room temperature for 1 hour. To the reaction mixture were added 30 ml of ethyl acetate and 20 ml of water, and phase separation was conducted. The organic layer was washed with 20 ml of a saturated aqueous sodium chloride solution, dried and subjected to distillation to remove the solvent. The residue was purified by silica gel column chromatography (eluent: dichloromethane/n-hexane=2/1 by v/v) to obtain 240 mg of 2-(3,4-diethoxyphenyl)-4-(3-methoxymethoxycarbonyl-4-hydroxy-5-vinylphenyl)thiazole (A) and 120 mg of 2-(3,4-diethoxyphenyl)-4-(3-methoxymethoxycarbonyl-4-methoxymethoxy-5-vinylphenyl)thiazole (B).

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hour
  2. stirringThe mixture was stirred at the same temperature for 2 hours and at room temperature for 1 hour
  3. additionTo the reaction mixture were added
  4. custom30 ml of ethyl acetate and 20 ml of water, and phase separation
  5. washThe organic layer was washed with 20 ml of a saturated aqueous sodium chloride solution
  6. customdried
  7. distillationsubjected to distillation
  8. customto remove the solvent
  9. customThe residue was purified by silica gel column chromatography (eluent: dichloromethane/n-hexane=2/1 by v/v)

Sources & evidence

ORD record
ord-d89c19702f024fec98673d0442b800b8
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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