Water → HCID 12980042, compound

HRID 1796578Notes

Reaction equation

HRID 1796578 reaction equation
[CH3:1][CH:2]([CH:4]=[O:5])[CH3:3].[CH:6]([C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[CH:12]=[C:11]([CH:18]([CH3:20])[CH3:19])[C:10]=1[S:21]Cl)([CH3:8])[CH3:7].O>C1COCC1>[CH3:1][C:2]([S:21][C:10]1[C:11]([CH:18]([CH3:19])[CH3:20])=[CH:12][C:13]([CH:15]([CH3:17])[CH3:16])=[CH:14][C:9]=1[CH:6]([CH3:8])[CH3:7])([CH3:3])[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 6561IsobutyraldehydeHCID 109126062,4,6-triisopropylphenylsulfenyl chloride

Product 1

HCID 12980042HCID 12980042, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of KH (383 mg, 9.5 mmol, Aldrich; washed with hexanes to remove oil and dried in vacuum) in THF (10 mL) was added dropwise isobutyric aldehyde (0.79 mL, 8.7 mmol, Aldrich) in THF (3 mL). The suspension was stirred for 25 min at RT under Ar (evolution of H2). A solution of 2,4,6-triisopropylphenylsulfenyl chloride (2.35 g, 8.7 mmol) in THF (10 mL) was then added at once. The color immediately changed from red to yellow. The solution was stirred at RT for 10 min, water (20 mL) was added to the reaction mixture under Ar (caution —H2 evolution). The solution was extracted with ethyl ether (2×30 mL), the extracts were dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel (13×4.3 cm) in toluene/hexane 1/5 followed by 1/4. Fractions containing the product were evaporated to give a light yellow oil that slowly crystallized, m=2.034 g (68.5%). Rf=0.33 (toluene/hexane 1/3). 1H NMR (CDCl3) 9.34 (s, 1H); 7.00 (s, 2H); 3.85 (septet, 2H; J=6.9 Hz); 2.86 (septet, 1H; J=6.9 Hz); 1.29 (s, 6H); 1.24 (d, 6H; J=6.9 Hz); 1.18 (unresolved broad d, 12H).

Workup

  1. stirringThe solution was stirred at RT for 10 min
  2. extractionThe solution was extracted with ethyl ether (2×30 mL)
  3. dry with materialthe extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel (13×4.3 cm) in toluene/hexane 1/5
  7. additionFractions containing the product
  8. customwere evaporated
  9. customto give a light yellow oil that
  10. customslowly crystallized

Sources & evidence

ORD record
ord-5816d2fc7aef45839ee2c340a8aa387b
Source dataset
uspto-grants-2006_04
Patent number
US07030200B2

Reaction notes

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