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

HRID 2308879Notes

Reaction equation

HRID 2308879 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-144d867e0f584164993b2dd8d1a1fec4
Source dataset
uspto-grants-1987_09
Patent number
US04691027

Reaction notes

Loading…