Sodium benzenethiolate → 1-Phenylmercapto-2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaene

HRID 1248338Notes

Reaction equation

HRID 1248338 reaction equation
C(O[CH2:5][C:6]([CH3:27])=[CH:7][CH:8]=[C:9]([CH3:26])[CH:10]=[CH:11][CH:12]=[C:13]([CH3:25])[CH:14]=[CH:15][C:16]1[C:21]([CH3:23])([CH3:22])[CH2:20][CH2:19][CH2:18][C:17]=1[CH3:24])(=O)C.[S-:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[Na+]>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C.C(OCC)C>[C:29]1([S:28][CH2:5][C:6]([CH3:27])=[CH:7][CH:8]=[C:9]([CH3:26])[CH:10]=[CH:11][CH:12]=[C:13]([CH3:25])[CH:14]=[CH:15][C:16]2[C:21]([CH3:22])([CH3:23])[CH2:20][CH2:19][CH2:18][C:17]=2[CH3:24])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 2

HCID 4110039Sodium benzenethiolateHCID 544237292,5,9-Trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaenyl acetate

Product 1

HCID 536691651-Phenylmercapto-2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaene

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

To a solution of 1.85 g (5 mmol) of 2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaenyl acetate in 25 ml of anhydrous THF and 8 ml of HMPA is added in portions 0.68 g (5.2 mmol) of sodium thiophenoxide. The resulting mixture is stirred at room temperature for 18 hours and then taken up in 250 ml of diethyl ether. The solution is washed with saturated aqueous NH4Cl and water, dried and evaporated in vacuo to give an oil. Purification on a silica gel dry column gives the desired product.

Workup

  1. washThe solution is washed with saturated aqueous NH4Cl and water
  2. customdried
  3. customevaporated in vacuo
  4. customto give an oil
  5. customPurification on a silica gel
  6. customdry column

Sources & evidence

ORD record
ord-43573024f9ea4962ab868ea97aca914e
Source dataset
uspto-grants-1985_06
Patent number
US04523042

Reaction notes

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