Triethylamine → HCID 64293806, compound

HRID 1470222Notes

Reaction equation

HRID 1470222 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[CH3:19][S:20]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 357781Ethyl 6-hydroxyhexanoate

Product 1

HCID 64293806HCID 64293806, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 6-hydroxyhexanoate (5 g, 31.2 mmol) in anhydrous dichloromethane (115 mL) under nitrogen at −10° C. was added triethylamine (8.7 mL, 62.5 mmol) followed by methanesulfonyl chloride (4.8 mL, 62.5 mmol) dropwise over 1 hour. The resulting solution was stirred at room temperature for 6 hours and then diluted to 300 mL using dichloromethane. The solution was washed with twice saturated NaHCO3, and the aqueous layers backextracted with dichloromethane. The combined organics were dried over MgSO4, filtered, and concentrated. The resulting dark orange oil was purified by column chromatography (column 5″L×2″W; eluted with a gradient of 100% hexanes→10%→20% ethyl acetate in hexanes) to afford the product as a pale yellow oil.

Workup

  1. additiondiluted to 300 mL
  2. washThe solution was washed with twice saturated NaHCO3
  3. dry with materialThe combined organics 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-d52f9ba6a5274e2a84de46f6862c4c7a
Source dataset
uspto-grants-2015_04
Patent number
US09006417B2

Reaction notes

Loading…