Hexane → HCID 9906375, compound

HRID 1602091Notes

Reaction equation

HRID 1602091 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][S:5][CH2:4][C:3]1=[O:8].C([Li])CCC.CCCCCC.[C:20]([C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:25]=1[OH:35])([CH3:23])([CH3:22])[CH3:21]>O1CCCC1.[Ag]=O>[CH3:23][C:20]([C:24]1[CH:29]=[C:28]([CH2:30][CH:4]2[S:5][CH2:6][CH2:7][N:2]([CH3:1])[C:3]2=[O:8])[CH:27]=[C:26]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:25]=1[OH:35])([CH3:21])[CH3:22]

Participants

7

Reactant 4

HCID 8058HexaneHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 136063494-Methylthiomorpholin-3-oneHCID 178418339Butyllithium

Product 1

HCID 9906375HCID 9906375, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

4-methyl-3-thiomorpholinone (1.88 g, 14.3 mmol) dissolved in tetrahydrofuran (72 ml) was cooled to 0° C. and treated with 1.37M n-butyl lithium in hexane (20.9 ml, 28.7 mmol). After five minutes, the cold bath was removed. Ten minutes later a solution of 2,6-di-t-butyl-quinone methide, prepared by adding silver oxide (33.2 g, 143 mmol) to 2,6-di-t-butyl-4-methyl-phenol (BHT) (3.16 g, 14.3 mmol) in tetrahydrofuran (72 ml) stirring for 30 minutes and filtering, was added dropwise over 20 min. The reaction was stirred for three hours, quenched with 1N hydrochloric acid, and evaporated to an aqueous suspension. The crude product was extracted into ethyl acetate, dried over sodium sulfate and concentrated in vacuo. Chromatography on silica gel eluting with 8 L of a 0-50% ethyl acetate in hexane gradient yielded desired product (2.0 g, 40%):

Workup

  1. customthe cold bath was removed
  2. customTen minutes later a solution of 2,6-di-t-butyl-quinone methide, prepared
  3. filtrationfiltering
  4. additionwas added dropwise over 20 min
  5. stirringThe reaction was stirred for three hours
  6. customquenched with 1N hydrochloric acid
  7. customevaporated to an aqueous suspension
  8. extractionThe crude product was extracted into ethyl acetate
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5c17593911041f0b24943f1e1a82018
Source dataset
uspto-grants-1999_11
Patent number
US05981523

Reaction notes

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