Tetrahydrofuran → HCID 86733508, compound

HRID 1657553Notes

Reaction equation

HRID 1657553 reaction equation
CO[C:3]1[CH:8]=CC(S(CC(C)=CCO)(=O)=O)=[CH:5][CH:4]=1.O1CCCC1.C([Li])CCC.Cl[CH2:29][CH:30]=[C:31](C)[CH:32]=[CH:33][C:34]1[C:39]([CH3:41])([CH3:40])[CH2:38][CH2:37][CH2:36][C:35]=1[CH3:42]>CCCCCC.O>[CH3:42][C:35]1[CH2:36][CH2:37][CH2:38][C:39]([CH3:40])([CH3:41])[C:34]=1[CH:33]=[CH:32][CH:31]=[CH:30][CH2:29][CH2:8][CH:3]=[CH:4][CH3:5]

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 54063363HCID 54063363, compoundHCID 540661274-(4-Methoxybenzene-1-sulfonyl)-3-methylbut-2-en-1-olHCID 178418339Butyllithium

Product 1

HCID 86733508HCID 86733508, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of 1.28 g. of 1-(p-methoxyphenylsulfonyl)-2-methyl-4-hydroxy-but-2-ene in 15 ml. of tetrahydrofuran (THF) was added at -70°C. 4.25 ml. of 2.37 M solution of n-butyllithium in hexane. The mixture was stirred at -70°C. for 30 minutes and a solution of 1.78 g. of 1-chloro-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)-penta-2,4-diene in 5 ml. of THF was added at -70°C. The solution was stirred at -70°C. for 50 minutes and allowed to warm to 70°C. The mixture was poured into water and extracted with diethyl ether. The extracts were washed with water, dried and concentrated to give 2.6 g. of 1-hydroxy-3,7-dimethyl-4-(p-methoxyphenyl-sulfonyl)-9-(2,6,6-trimethylcyclohexen-1-yl)-nona-2,6,8-triene which was chromatographed on silica get to give 0.48 g. of 1-hydroxy-3,7-dimethyl-4-p-methoxyphenylsulfonyl)-9-(2,6,6-trimethylcyclohexen-1-yl)-nona-2,6,8-triene (20% yield) having a UV in isopropanol at λmax = 241-2 mμ (ε24,625).

Workup

  1. stirringThe solution was stirred at -70°C. for 50 minutes
  2. temperatureto warm to 70°C
  3. extractionextracted with diethyl ether
  4. washThe extracts were washed with water
  5. customdried
  6. concentrationconcentrated
  7. customto give 2.6 g
  8. customof 1-hydroxy-3,7-dimethyl-4-(p-methoxyphenyl-sulfonyl)-9-(2,6,6-trimethylcyclohexen-1-yl)-nona-2,6,8-triene which was chromatographed on silica
  9. customget
  10. customto give 0.48 g

Sources & evidence

ORD record
ord-a76c4e26b0b148aea3b3664415c6b7ff
Source dataset
uspto-grants-1976_06
Patent number
US03960967

Reaction notes

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