Triethylamine → HCID 57458019, compound

HRID 1013093Notes

Reaction equation

HRID 1013093 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:9]([CH2:10][CH2:11][OH:12])=[CH:8][CH:7]=[CH:6][C:5]=1[O:13][CH3:14].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:22][S:23]([O:1][CH2:2][CH2:3][C:4]1[C:9]([CH2:10][CH2:11][O:12][S:23]([CH3:22])(=[O:25])=[O:24])=[CH:8][CH:7]=[CH:6][C:5]=1[O:13][CH3:14])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 57458018HCID 57458018, compound

Product 1

HCID 57458019HCID 57458019, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a slurry of 2,3-bis-(2-hydroxyethyl)-1-methoxybenzene (50.6 g, 0.258 mol, 1 equiv.) and triethylamine (78.3 g, 0.774 mol, 3 equiv.) in DCM (500 mL) at 0° C., add dropwise a solution of methanesulfonyl chloride (65.0 g, 0.567 mol, 2.2 equiv.) in DCM (100 mL) over 45 min. The addition is exothermic and the methanesulfonyl chloride is added at a rate to keep the temperature below 10° C. After the addition is complete, warm the reaction to RT. Wash the solution with water (2×500 mL), and then brine (750 mL). Dry (sodium sulfate) and concentrate to give the title compound as a dark yellow oil (87.4 g, 96.2%), which is used in the next reaction without further purification. An analytical sample is obtained utilizing silica gel chromatography, eluting with 100% diethyl ether.

Workup

  1. additionThe addition
  2. customthe temperature below 10° C
  3. additionAfter the addition
  4. temperaturewarm
  5. customthe reaction to RT
  6. washWash the solution with water (2×500 mL)
  7. dry with materialDry (sodium sulfate)
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-f21f2601f36b45bea0eb243695291fcf
Source dataset
uspto-grants-2011_07
Patent number
US07981882B2

Reaction notes

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