Water → HCID 178427788, compound

HRID 2380570Notes

Reaction equation

HRID 2380570 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][C@H:13]1[CH2:16][C@H:15]([CH2:17][OH:18])[CH2:14]1.O.CCCCCC.C(OCC)(=O)C>N1C=CC=CC=1>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:12][C@H:13]2[CH2:16][C@H:15]([CH2:17][OH:18])[CH2:14]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 21226206Ethyl acetate hexaneHCID 178521039HCID 178521039, compound

Product 1

HCID 178427788HCID 178427788, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

p-Toluenesulfonyl chloride (3.47 g, 18.2 mmol) was added to a solution of the above preparation of (trans)-3-hydroxycyclobutanemethanol, benzoate ester (2.5 g) in dry pyridine (35 ml) under nitrogen, and the mixture was stirred at 60° for 18 hours. Water (20 ml) was added, and heating was continued for 4 hours longer. The reaction was cooled to room temperature and concentrated in vacuo to a solid, which was dissolved in ethyl acetate and water. The ethyl acetate layer was washed with water, saturated aqueous NaHCO3, and water, dried (Na2SO4), and concentrated to a solid (3.8 g). This solid was combined with 1.5 g of solid from a similar preparation. Chromatography of these solids over 200 g of LP-1 silica gel, using hexane-ethyl acetate (6:1), gave (trans)-3-[[(4-methylphenyl)sulfonyl]oxy]cyclobutanemethanol, benzoate ester containing varying amounts of its cis-isomer as shown below:

Workup

  1. temperatureheating
  2. waitwas continued for 4 hours
  3. concentrationconcentrated in vacuo to a solid, which
  4. dissolutionwas dissolved in ethyl acetate
  5. washThe ethyl acetate layer was washed with water, saturated aqueous NaHCO3, and water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated to a solid (3.8 g)
  8. customThis solid was combined with 1.5 g of solid from a similar preparation

Sources & evidence

ORD record
ord-edfed29610324df7910b64edb63d1d9a
Source dataset
uspto-grants-1994_11
Patent number
US05369098

Reaction notes

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