Hydrochloric Acid → HCID 14989157, compound

HRID 1722802Notes

Reaction equation

HRID 1722802 reaction equation
[CH3:1][C:2]([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])([CH3:4])[CH3:3].[CH:21]([Mg]Cl)([CH3:23])[CH3:22].Cl.O>O1CCCC1>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([S:16][CH2:17][CH2:18][CH:19]([OH:20])[CH:21]([CH3:23])[CH3:22])[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]=1[OH:11])([CH3:1])[CH3:3]

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 14989157HCID 14989157, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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 2M 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. 2N 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. Analysis calc. for C20H34O2S(338.54):

Workup

  1. additionhad previously been added under argon gas to a flask that
  2. customhad been dried in vacuo overnight
  3. customReaction temperature
  4. temperaturewas maintained at 10°-15° C. with an ice bath
  5. additionWhen addition
  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-705fc44fd6784c2b8db0a66e4a13135a
Source dataset
uspto-grants-1989_08
Patent number
US04857558

Reaction notes

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