Iodine → 5-Formyloxy-2-(3-iodopropyl)-4,6,7-trimethyl-1,3-benzoxathiole

HRID 2350993Notes

Reaction equation

HRID 2350993 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:20]I.[OH:22][C:23]1[C:24]([CH3:38])=[C:25]([CH3:37])[C:26]2[O:30][CH:29]([CH2:31][CH2:32][CH2:33]O)[S:28][C:27]=2[C:35]=1[CH3:36].O.CN(C)[CH:42]=[O:43]>C1C=CC=CC=1.C1CCCCC1>[CH:42]([O:22][C:23]1[C:24]([CH3:38])=[C:25]([CH3:37])[C:26]2[O:30][CH:29]([CH2:31][CH2:32][CH2:33][I:20])[S:28][C:27]=2[C:35]=1[CH3:36])=[O:43]

Participants

8

Reactant 5

HCID 807IodineHCID 962WaterHCID 6228DimethylformamideHCID 11776TriphenylphosphineHCID 1275772-(3-Hydroxypropyl)-4,6,7-trimethyl-2H-1,3-benzoxathiol-5-ol

Product 1

HCID 135920615-Formyloxy-2-(3-iodopropyl)-4,6,7-trimethyl-1,3-benzoxathiole

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8078CyclohexaneSolvent

Procedure

1.5 g of triphenylphosphine and 1.5 g of iodine were dissolved in 5 ml of dimethylformamide, and the solution was stirred for 30 minutes at room temperature, after which 0.5 g of 3-(5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiole-2-yl)propanol (prepared as described in Example 71) was added, and the reaction mixture was allowed to react for 20 hours at room temperature. The reaction mixture was then poured into water and extracted with benzene. The extract was washed with water and dried over anhydrous sodium sulfate, and the benzene was distilled off under reduced pressure. The resulting crude product was subjected to silica gel column chromatography and the final reaction products were fractionated using a 1:2 by volume mixture of cyclohexane and benzene. The desired 5-formyloxy-2-(3-iodopropyl)-4,6,7-trimethyl-1,3-benzoxathiole, melting at 91°-93° C., was obtained from the fraction first eluted. Mass spectrum (m/e): 392 (M+).

Workup

  1. customto react for 20 hours at room temperature
  2. extractionextracted with benzene
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe benzene was distilled off under reduced pressure
  6. customthe final reaction products

Sources & evidence

ORD record
ord-fccefc5327164c8292a157b17ceaac22
Source dataset
uspto-grants-1989_10
Patent number
US04871762

Reaction notes

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