HCID 54512866, compound → HCID 54521914, compound

HRID 1580738Notes

Reaction equation

HRID 1580738 reaction equation
Br[CH2:2][C:3]([CH3:16])=[CH:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]2[O:11][CH2:12][O:13][C:9]=2[CH:8]=1.[Na].[CH2:18]([S:22][O-])[CH:19]([CH3:21])[CH3:20]>C1C=CC=CC=1>[CH2:18]([S:22][CH2:2][C:3]([CH3:16])=[CH:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]2[O:11][CH2:12][O:13][C:9]=2[CH:8]=1)[CH:19]([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 54512866HCID 54512866, compoundHCID 86732997HCID 86732997, compound

Product 1

HCID 54521914HCID 54521914, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 4.3 g (0.015 mol) of 5-(4-bromo-3-methyl-2-butenyloxy)-1,3-benzodioxol in 50 cc of benzene is added at 25° to 1.7 g (0.015 mol) of sodium-isobutylthio alcoholate in 30 cc of benzene The mixture is kept at reflux temperature for 13 hours, is subsequently filtered, washed with saturated salt solution and evaporated. The remaining yellow oil is chromatographed with hexane/ethyl acetate 7 : 1 on silica gel, whereby colourless 5-(4-isobutylthio-3-methyl-2-butenyloxy)-1,3-benzodioxol is obtained. nD20 = 1.5463.

Workup

  1. temperatureat reflux temperature for 13 hours
  2. filtrationis subsequently filtered
  3. washwashed with saturated salt solution
  4. customevaporated
  5. customThe remaining yellow oil is chromatographed with hexane/ethyl acetate 7 : 1 on silica gel

Sources & evidence

ORD record
ord-39a099f1e3f74320bb3b2d7aa2384d69
Source dataset
uspto-grants-1976_01
Patent number
US03933804

Reaction notes

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