Pyridine → HCID 178418683, compound

HRID 1707909Notes

Reaction equation

HRID 1707909 reaction equation
O1CCCCC1[O:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1.S(O[Si](C)(C)C)(O[Si](C)(C)C)(=O)=O.N1C=CC=CC=1>CO.C(OCC)C.ClCCl>[CH2:26]([C:23]1[CH:22]=[CH:21][C:20]([C:17]2[CH:16]=[CH:15][C:14]([C@H:11]3[CH2:12][CH2:13][C@H:8]([OH:7])[CH2:9][CH2:10]3)=[CH:19][CH:18]=2)=[CH:25][CH:24]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

7

Reactant 3

HCID 1049PyridineHCID 87573Silanol, trimethyl-, 1,1'-sulfateHCID 178418673HCID 178418673, compound

Product 1

HCID 178418683HCID 178418683, compoundYield 50.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.2 g of trans-4-(4'-decyl-4-biphenylyl)cyclohexyl tetrahydropyranyl ether in 40 ml of methanol and 2 ml of diethyl ether was treated with a solution of 7.3 mg of bistrimethylsilyl sulfate in 2 ml of dichloromethane. The reaction mixture was stirred at room temperature for 2 hours and then treated with 0.2 ml of pyridine. Subsequently, the reaction mixture was concentrated and the residue was then taken up in 50 ml of dichloromethane, washed twice with water, dried over magnesium sulfate, filtered and again concentrated. The residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9;1). Recrystallization from methanol gave 0.5 g of trans-4-(4'-decyl-4-biphenylyl)cyclohexanol.

Workup

  1. concentrationSubsequently, the reaction mixture was concentrated
  2. washwashed twice with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationagain concentrated
  6. customThe residue was purified by chromatography on silica gel with toluene/ethyl acetate (vol. 9;1)
  7. customRecrystallization from methanol

Sources & evidence

ORD record
ord-b3c2d20cf643482aa86ad5eeaa7ebf65
Source dataset
uspto-grants-1994_10
Patent number
US05356563

Reaction notes

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