Triethylamine → HCID 59511924, compound

HRID 1157661Notes

Reaction equation

HRID 1157661 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]1([CH:12]([OH:19])[CH2:13][CH2:14][CH:15]([OH:18])[CH2:16][CH3:17])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:18][CH:15]([CH2:16][CH3:17])[CH2:14][CH2:13][CH:12]([O:19][S:2]([CH3:1])(=[O:4])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59511933HCID 59511933, compound

Product 1

HCID 59511924HCID 59511924, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

Stir methanesulfonyl chloride (2.94 g, 25.7 mmol) in dichloromethane (40 mL) in a flask that has been purged with nitrogen. Cool the mixture to −20° C. and add 1-phenyl-hexane-1,4-diol (2.0 g, 10.3 mmol) dissolved in dichloromethane (5 mL), and triethylamine (3.13 g, 30.9 mmol). After 2 h of stirring at −20° C., quench with saturated aqueous NH4Cl solution and concentrate to a quarter of the volume. Dilute with EtOAc, and wash with saturated NaHCO3 solution, water, and brine. Dry the organic portion over Na2SO4, filter, and concentrate to obtain 3.0 g (83%) of the title compound. Use with no further purification. 1H NMR (400 MHz, CD3OD): δ 7.37-7.24 (m, 5H), 4.69-4.59 (m, 1H), 4.21-4.14 (m, 1H), 3.01 (s, 3H), 2.73 (s, 3H), 1.91-1.55 (m, 6H), 0.96-0.88 (m, 3H).

Workup

  1. customhas been purged with nitrogen
  2. customquench with saturated aqueous NH4Cl solution
  3. concentrationconcentrate to a quarter of the volume
  4. additionDilute with EtOAc
  5. washwash with saturated NaHCO3 solution, water, and brine
  6. dry with materialDry the organic portion over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-dfebfcb6a47c449eb83e71923c1aefb3
Source dataset
uspto-grants-2010_10
Patent number
US07807691B2

Reaction notes

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