Hydrochloric Acid → HCID 131716999, compound

HRID 728400Notes

Reaction equation

HRID 728400 reaction equation
CC([C:5]1[CH:6]=[C:7]([S:16][CH2:17][CH2:18][CH:19]=[O:20])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])(C)C.[CH:21]([Mg]Cl)([CH3:23])[CH3:22].Cl.O>O1CCCC1>[CH3:15][C:12]([C:9]1[CH:8]=[C:7]([S:16][CH2:17][CH2:18][CH:19]([OH:20])[CH:21]([CH3:23])[CH3:22])[CH:6]=[CH:5][C:10]=1[OH:11])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 140118163-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanalHCID 178418918HCID 178418918, compound

Product 1

HCID 131716999HCID 131716999, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
12.5 °C

Procedure

2.0 g of the aldehyde of Example 4 was dissolved in 20 ml of dry tetrahydrofuran under argon and added to 8.5 ml of 2 M isopropylmagnesium chloride in tetrahydrofuran that had previously been added under argon gas to a flask that had been dried in vacuo overnight. Reaction temperature was maintained at 10-15° C. with an ice bath. When addition was complete, the reaction mixture was allowed warm to room temperature and stirred for 3 hours. 2 N hydrochloric acid (2 ml) was added followed by 50 ml of water and the mixture extracted with ethyl acetate three times. The organic extracts were combined, washed with water twice and dried over sodium sulfate. The solvent was removed in vacuo after filtration and the crude product chromatographed on silica to give the title compound.

Workup

  1. additionhad previously been added under argon gas to a flask that
  2. customhad been dried in vacuo overnight
  3. customReaction temperature
  4. additionWhen addition
  5. temperaturethe reaction mixture was allowed warm to room temperature
  6. extractionthe mixture extracted with ethyl acetate three times
  7. washwashed with water twice
  8. dry with materialdried over sodium sulfate
  9. customThe solvent was removed in vacuo
  10. filtrationafter filtration
  11. customthe crude product chromatographed on silica

Sources & evidence

ORD record
ord-3adb96c99f324a88be5aee75f8430a8d
Source dataset
uspto-grants-1991_09
Patent number
US05047593

Reaction notes

Loading…