Methylene blue cation → HCID 131724432, compound

HRID 1582695Notes

Reaction equation

HRID 1582695 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](C)=[CH:15][CH2:16][OH:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CN(C1C=CC2N=C3C(=CC(C=C3)=[N+](C)C)SC=2C=1)C.[C:39]1(=[O:44])[CH2:43][CH2:42][CH2:41][CH2:40]1.[O:45]1[CH2:50]CCOO1>CC#N.Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH:14]=[CH:15][CH:16]3[CH2:50][O:45][C:39]4([CH2:43][CH2:42][CH2:41][CH2:40]4)[O:44][O:17]3)=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 4139Methylene blue cationHCID 8452CyclopentanoneHCID 19593658CID 19593658HCID 698003213-(4'-Chloro-[1,1'-biphenyl]-4-yl)-2-butenol2×

Product 1

HCID 131724432HCID 131724432, compoundYield 33.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of 3-(4′-chloro-[1,1′-biphenyl]4yl)-2-butenol (4g, 500 gm) and methylene blue (40 mg) in CH3CN (30 ml) was photooxygenated at 5° C. for 5 h. Cyclopentanone (0.5 ml) and hydrochloric acid (5 drops) were added and reaction mixture was stirred at r.t. for 1.5 h and then left at r.t for 48 h. The reaction mixture was concentrated. Crude product was purified by column chromatography to furnish 230 mg (33.8% yield, based on allylic alcohol, 4g used) of trioxane 7ga m.p. 105-107° C.

Workup

  1. customreaction mixture
  2. waitleft at r.t for 48 h
  3. concentrationThe reaction mixture was concentrated
  4. customCrude product was purified by column chromatography
  5. customto furnish 230 mg (33.8% yield

Sources & evidence

ORD record
ord-d2ff89d331d340feb13f1839295d1fb8
Source dataset
uspto-grants-2004_05
Patent number
US06737438B2

Reaction notes

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