Water → Ethyl 5-(1-(tosyloxy)ethyl)-1,3-dioxane-5-carboxylate

HRID 2176245Notes

Reaction equation

HRID 2176245 reaction equation
[OH:1][CH:2]([C:4]1([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:9][O:8][CH2:7][O:6][CH2:5]1)[CH3:3].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.O>N1C=CC=CC=1>[S:21]([O:1][CH:2]([C:4]1([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:9][O:8][CH2:7][O:6][CH2:5]1)[CH3:3])([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 85877287HCID 85877287, compound

Product 1

HCID 86706084Ethyl 5-(1-(tosyloxy)ethyl)-1,3-dioxane-5-carboxylateYield 76.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of ethyl 5-(1-hydroxyethyl)-1,3-dioxane-5-carboxylate (16.8 g, 83 mmol) in dry pyridine (40 mL) at 0° C. was added 4-toluenesulfonyl chloride (19.1 g, 99 mmol). The mixture was stirred at rt for 16 h. Water (40 mL) was added, and the mixture was extracted with ethyl acetate (2×400 mL). The organic layer was washed with brine (3×). After concentrated in vacuo, the crude product was purified by silica gel chromatography eluting with petroleum ether/ethyl acetate 25:1 to 5:1 to provide the title compound (22.7 g, 76%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 1.26 (m, 3H), 1.34 (d, J=6.8 Hz, 3H), 2.45 (s, 3H), 3.80 (d, J=11.6 Hz, 1H), 3.87 (d, J=11.6 Hz, 1H), 4.02 (d, J=11.6 Hz, 1H), 4.08 (d, J=12.0 Hz, 1H), 4.20-4.17 (m, 2H), 5.03-4.98 (m, 1H), 7.34 (d, J=8.0 Hz, 2H), 7.79 (d, J=8.8 Hz, 2H).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×400 mL)
  2. washThe organic layer was washed with brine (3×)
  3. concentrationAfter concentrated in vacuo
  4. customthe crude product was purified by silica gel chromatography
  5. washeluting with petroleum ether/ethyl acetate 25:1 to 5:1

Sources & evidence

ORD record
ord-39ba8c1400d8493aae1158afe9d5cae7
Source dataset
uspto-grants-2015_06
Patent number
US09062092B2

Reaction notes

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