Iodine → 2-(3-Iodopropyl)-5-methoxymethoxy-4,6,7-trimethyl-1,3-benzoxathiole

HRID 2351001Notes

Reaction equation

HRID 2351001 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([CH3:20])=[C:7]([CH3:19])[C:8]2[O:12][CH:11]([CH2:13][CH2:14][CH2:15]O)[S:10][C:9]=2[C:17]=1[CH3:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:40]I.O>C1C=CC=CC=1.N1C=CC=CC=1>[I:40][CH2:15][CH2:14][CH2:13][CH:11]1[S:10][C:9]2[C:17]([CH3:18])=[C:5]([O:4][CH2:3][O:2][CH3:1])[C:6]([CH3:20])=[C:7]([CH3:19])[C:8]=2[O:12]1

Participants

7

Reactant 4

HCID 807IodineHCID 962WaterHCID 11776TriphenylphosphineHCID 148021913-(5-Methoxymethoxy-4,6,7-trimethyl-1,3-benzoxathiole-2-yl)propanol

Product 1

HCID 148021922-(3-Iodopropyl)-5-methoxymethoxy-4,6,7-trimethyl-1,3-benzoxathiole

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent

Procedure

1.0 g of 3-(5-methoxymethoxy-4,6,7-trimethyl-1,3-benzoxathiole-2-yl)propanol (prepared as described in Example 85) was dissolved in a mixture of 15 ml of benzene and 1.5 ml of pyridine, and then 1.7 g of triphenylphosphine, followed by 1.7 g of iodine, was added to the solution. The mixture was stirred for 40 minutes at room temperature. The product was poured into water and extracted with benzene. The extract was washed with water and then dried over anhydrous sodium sulfate. The benzene was distilled off to yield a crude product, which was subjected to silica gel column chromatography. The title compound was obtained from the fraction eluted with benzene.

Workup

  1. additionwas added to the solution
  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
  6. customto yield a crude product, which

Sources & evidence

ORD record
ord-cdfdc6367d0144f1a6794c45ae8b8718
Source dataset
uspto-grants-1989_10
Patent number
US04871762

Reaction notes

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