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Bromine → 5-Methyl-2-[3-[2,6-dimethyl-4-(2-methyl-tetrazol-5-yl)phenoxy]-propyl]-2,5-dimethoxy-2,5-dihydrofuran

HRID 865694
Notes
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Reaction equation

HRID 865694 reaction equation
C(=O)([O-])[O-].[Na+].[CH3:6][C:7]1([O:32][CH3:33])[O:11][C:10]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[C:23]([CH3:24])=[CH:22][C:21]([C:25]3[N:26]=[N:27][N:28]([CH3:30])[N:29]=3)=[CH:20][C:19]=2[CH3:31])([O:12][CH3:13])[CH:9]=[CH:8]1.[Na+].CC1OC(CCCOC2C(C)=CC(C3N=NN(C)N=3)=CC=2C)=CC=1.BrBr>CO.[Cl-].[Na+].O>[CH3:6][C:7]1([O:32][CH3:33])[O:11][C:10]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[C:23]([CH3:24])=[CH:22][C:21]([C:25]3[N:26]=[N:27][N:28]([CH3:30])[N:29]=3)=[CH:20][C:19]=2[CH3:31])([O:12][CH3:13])[CH:9]=[CH:8]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24408BromineHCID 52730885-[3,5-Dimethyl-4-[3-(5-methyl-2-furyl)propoxy]phenyl]-2-methyl-tetrazoleHCID 677670605-Methyl-2-[3-[2,6-dimethyl-4-(2-methyl-tetrazol-5-yl)-phenoxy]-propyl]-2,5 dimethoxy-2,5-dihydrofuran Sodium carbonate

Product 1

HCID 229153545-Methyl-2-[3-[2,6-dimethyl-4-(2-methyl-tetrazol-5-yl)phenoxy]-propyl]-2,5-dimethoxy-2,5-dihydrofuranYield 87%

Reagents, catalysts & solvents

2
HCID 887MethanolSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

5-Methyl-2-[3-[2,6-dimethyl-4-(2-methyl-tetrazol-5-yl)-phenoxy]-propyl]-2,5 dimethoxy-2,5-dihydrofuran Sodium carbonate (1.2 g) was added to a cooled (-10° C.) solution of 5-methyl 2-[3-[2,6-dimethyl-4-(2-methyl-tetrazol-5-yl)-phenoxy]-propyl]furan from example 9d (780 mg, 2.4 mmol) in 18 mL of methanol with stirring, and then bromine (0.135 g, 14 mmol) in 8 mL of methanol was added dropwise until the brown color persisted, and the resulting reaction mixture was allowed to stir at -10° C. for 45 min. To the mixture was added brine, extracted with ether (3×25 mL), and the organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo to yield an oil which was purified by MPLC chromatography (ethyl acetate/hexane 3:7) to afford 820 mg (76.3%) of 5-methyl-2-[3-[2,6-dimethyl-4-(2-methyl-tetrazol-5-yl)-phenoxy]-propyl]-2,5-dimethoxy-2,5-dihyrofuran.

Workup

  1. customthe resulting reaction mixture
  2. stirringto stir at -10° C. for 45 min
  3. extractionextracted with ether (3×25 mL)
  4. washthe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto yield an oil which
  8. customwas purified by MPLC chromatography (ethyl acetate/hexane 3:7)

Sources & evidence

ORD record
ord-59e3da985c9f435f8506b6e61a2150e6
Source dataset
uspto-grants-1996_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05567717

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes