4-Toluenesulfonyl chloride → HCID 178472496, compound

HRID 237327Notes

Reaction equation

HRID 237327 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][CH:13]([CH2:16][OH:17])[CH2:14][OH:15])[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>ClCCl>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][CH:13]([CH2:16][OH:17])[CH2:14][O:15][S:31]([C:28]2[CH:29]=[CH:30][C:25]([CH3:35])=[CH:26][CH:27]=2)(=[O:33])=[O:32])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 178472495HCID 178472495, compound

Product 1

HCID 178472496HCID 178472496, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of cis/trans-4-(2-hydroxy-1-hydroxymethyl-ethoxy)-cyclohexanecarboxylic acid ethyl ester (3:7) (0.74 g, 3.0 mmol) and triethylamine (0.42 ml, 3.0 mmol) in dichloromethane (30 ml) a catalytic amount of 4-N,N-dimethylaminopyridine was added. A solution of p-toluenesulfonyl chloride (0.57 g, 3.0 mmol) in dichloromethane (10 ml) was added dropwise at room temperature. Stirring for 16 h was followed by partitioning between ethyl acetate (100 ml) and 0.5 M aqueous hydrogen chloride solution (50 ml). The layers were separated. The aqueous layer was extracted with two portions of ethyl acetate. The combined organic layers were washed with one portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Flash-chromatography with n-heptane/ethyl acetate as eluent gave the title compound (0.46 g, 38%) as colorless oil. MS m/e: 401 (M+H+)

Workup

  1. customby partitioning between ethyl acetate (100 ml) and 0.5 M aqueous hydrogen chloride solution (50 ml)
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with two portions of ethyl acetate
  4. washThe combined organic layers were washed with one portion of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a1008b8bf5e4ab3ad4ee7f549183bcb
Source dataset
uspto-grants-2014_02
Patent number
US08642590B2

Reaction notes

Loading…