HCID 54512866, compound → HCID 54521914, compound

HRID 918008Notes

Reaction equation

HRID 918008 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-040c70935eeb41af9a7438f389e9d46e
Source dataset
uspto-grants-1976_07
Patent number
US03968235

Reaction notes

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