Sodium Iodide → HCID 54238241, compound

HRID 653116Notes

Reaction equation

HRID 653116 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH2-:21][C:22]([CH3:24])=[O:23].S(O[CH2:36][C@H:37]([OH:40])[CH2:38]O)(C1C=CC(C)=CC=1)(=O)=O.[Na+].[I-]>CN(C=O)C>[CH3:21][C:22]1([CH3:24])[O:40][C@@H:37]([CH2:38][O:1][C:2]2[CH:18]=[CH:17][C:5]([C:6]([C:8]3[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=3)=[O:7])=[CH:4][CH:3]=2)[CH2:36][O:23]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 110968174-Hydroxy-4'-nitrobenzophenoneHCID 178427771HCID 178427771, compound

Product 1

HCID 54238241HCID 54238241, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g of 4-hydroxy-4'-nitrobenzophenone was added to 8 ml of DMF containing 110 mg of NaH. The mixture was heated at 40°-50° C. for 30 minutes, then treated with 1.29 g of (R)-3-tosyloxy-1,2-propanediol acetonide and a trace of NaI and heated at 150° C. (oil-bath) under argon for 4 hours. After working-up and purification there were obtained 930 mg (64%) of 4-[[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-4'-nitrobenzophenone, m.p. 92°-93° C., [α]D20 +5.3° (c 1%, MeOH).

Workup

  1. temperatureThe mixture was heated at 40°-50° C. for 30 minutes
  2. custompurification there

Sources & evidence

ORD record
ord-25f45df5468c46bbb9b2cb6266a7a536
Source dataset
uspto-grants-1987_06
Patent number
US04675328

Reaction notes

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