Water → HCID 18669129, compound

HRID 1058752Notes

Reaction equation

HRID 1058752 reaction equation
[CH:1]1([O:6][CH2:7][CH2:8][OH:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.O>ClCCl>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([O:9][CH2:8][CH2:7][O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 131875202-(Cyclopentyloxy)ethan-1-ol

Product 1

HCID 18669129HCID 18669129, compoundYield 572.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(cyclopentyloxy)-1-ethanol (prepared as described in J. Org. Chem., 1968, 33, 2271-2284: 127 mg, 0.97 mmol) and triethylamine (101 mg, 0.1 mmol) in dichloromethane (3 mL) at 0° C. was added 4-bromobenzenesulfonyl chloride (255 mg, 0.1 mmol) in dichloromethane (2 mL) dropwise over 5 minutes. The reaction was then warmed to room temperature and stirred for 16 hours. The mixture was then poured into water (3 mL) and the two layers were separated. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give a crude residue. This was purified by column chromatography on silica gel (50 g), eluting with a gradient of dichloromethane:hexane (50:50 to 0:100), to give the title compound (200 mg, 59%) as a colourless oil.

Workup

  1. customthe two layers were separated
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a crude residue
  6. customThis was purified by column chromatography on silica gel (50 g)
  7. washeluting with a gradient of dichloromethane:hexane (50:50 to 0:100)

Sources & evidence

ORD record
ord-4aa52edeff9544e7867fa02b06c49da3
Source dataset
uspto-grants-2003_02
Patent number
US06518282B1

Reaction notes

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