Triethylamine → HCID 57500205, compound

HRID 537822Notes

Reaction equation

HRID 537822 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[CH3:23][S:24]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19788674Benzyl 5-hydroxypentanoate

Product 1

HCID 57500205HCID 57500205, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzyl 5-hydroxypentanoate (2.01 g, 9.65 mmol) in anhydrous dichloromethane (30 mL) under nitrogen at −15° C. was added triethylamine (2.7 mL, 19.3 mmol) followed by a solution of methanesulfonyl chloride (1.5 mL, 19.3 mmol) dropwise over 20 minutes. The reaction was stirred at room temperature overnight and then diluted to 75 mL using dichloromethane. The organic layer was washed three times with saturated NaHCO3 and the combined aqueous layers backextracted with dichloromethane. The combined organic phases were dried over MgSO4, filtered, and concentrated. The resulting dark orange oil was purified by column chromatography (column 5″L×1″W; eluted with a gradient of 100% hexanes→10%→20%→25% diethyl ether in hexanes) to afford the product as a pale yellow oil (1.39 g, 50%).

Workup

  1. additiondiluted to 75 mL
  2. washThe organic layer was washed three times with saturated NaHCO3
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting dark orange oil was purified by column chromatography (column 5″L×
  7. washeluted with a gradient of 100% hexanes

Sources & evidence

ORD record
ord-2ac271ab4d374233b02e9f3882455f76
Source dataset
uspto-grants-2014_10
Patent number
US08865675B2

Reaction notes

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