4-Toluenesulfonyl chloride → HCID 178427750, compound

HRID 2209389Notes

Reaction equation

HRID 2209389 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C@H:14]2[CH2:19][CH2:18][C@H:17]([CH2:20][OH:21])[CH2:16][CH2:15]2)[CH2:10][CH2:9]1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>N1C=CC=CC=1.C(Cl)Cl>[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28]([O:21][CH2:20][C@H:17]2[CH2:18][CH2:19][C@H:14]([C@H:11]3[CH2:10][CH2:9][C@H:8]([CH2:7][CH2:6][CH:2]4[O:3][CH2:4][CH2:5][O:1]4)[CH2:13][CH2:12]3)[CH2:15][CH2:16]2)(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 178520952HCID 178520952, compound

Product 1

HCID 178427750HCID 178427750, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2.96 g of crude [trans-4-[trans-4-(2-(1,3-dioxolan-2-yl)ethyl)cyclohexyl]cyclohexyl]methanol in 20 ml of dry pyridine is treated at 0° C. with 2.1 g of p-toluenesulfonyl chloride. The mixture is stirred at room temperature for 15 hours, then diluted with 200 ml of methylene chloride and washed several times with water. The organic phase is dried over magnesium sulfate, filtered and evaporated. Chromatographic purification of the resulting crude product on silica gel with ethyl acetate/petroleum ether (vol. 1:9) gives [trans-4-[trans-4-(2-(1,3-dioxolan-2-yl)ethyl)cyclohexyl]cyclohexyl]methyl p-toluenesulfonate.

Workup

  1. washwashed several times with water
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customChromatographic purification of the resulting crude product on silica gel with ethyl acetate/petroleum ether (vol. 1:9)

Sources & evidence

ORD record
ord-3f12e3e2cb774768bca0d545117f4f40
Source dataset
uspto-grants-1995_10
Patent number
US05454974

Reaction notes

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