Water → (e)-1,4-Ditosyloxy-2-butene

HRID 1698751

Reaction equation

HRID 1698751 reaction equation
[CH2:1]([OH:6])/[CH:2]=[CH:3]/[CH2:4][OH:5].[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[CH3:18][C:19]([CH3:22])([O-])[CH3:20].[Na+].[OH2:24]>C1COCC1>[S:13]([O:5][CH2:4]/[CH:3]=[CH:2]/[CH2:1][O:6][S:13]([C:10]1[CH:11]=[CH:22][C:19]([CH3:20])=[CH:18][CH:9]=1)(=[O:14])=[O:24])([C:10]1[CH:11]=[CH:12][C:7]([CH3:17])=[CH:8][CH:9]=1)(=[O:15])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 175854trans-2-Butene-1,4-diolHCID 23676156Sodium t-butoxide

Product 1

HCID 18320921(e)-1,4-Ditosyloxy-2-buteneYield 182%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (E)-2-buten-1,4-diol (326 mg, 3.7 mmol) and p-toluenesulfonyl chloride (1.76 g, 9.25 mmol) in 30 mL of THF was added portionwise sodium tert-butoxide (1.07 g, 11.1 mmol)) under stirring at 0° C. The mixture was then stirred overnight at rt. Water (100 mL) was added and the product was extracted with CH2CL2 (3×25 mL). The extract was dried with MgSO4, filtered, and evaporated. Purification by flash column chromatography with hexane:ether:CH2CH2/3:1:1 gave the product as a crystal (1.21 g, 182%), m.p. 90-91° C. 1H NMR (300 MHz, CDCl3) δ 7.77 (d, J=8.7 Hz, 4H), 7.35 (d, J−8.4 Hz, 4H), 5.75-5.73 (m, 2H), 4.49-4.47 (m, 4H), 2.46 (s, 6H; Anal. Calcd for C18H20O6S2: C, 54.53; H, 5,08,found C, 54.61; H, 5.07.

Workup

  1. stirringThe mixture was then stirred overnight at rt
  2. extractionthe product was extracted with CH2CL2 (3×25 mL)
  3. dry with materialThe extract was dried with MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash column chromatography with hexane

Sources & evidence

ORD record
ord-c47b6ed2961c4c2db566355e29457ec2
Source dataset
uspto-grants-2002_02
Patent number
US06344179B1

Linked notes

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