Propylene Glycol → HCID 13777645, compound

HRID 338550Notes

Reaction equation

HRID 338550 reaction equation
[CH2:1]([OH:5])[CH:2]([OH:4])[CH3:3].[C:6](Cl)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>ClCCl.O>[CH3:33][S:34]([O:4][CH:2]([CH3:3])[CH2:1][O:5][C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:36])=[O:35]

Participants

7

Reactant 4

HCID 1030Propylene GlycolHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 13777645HCID 13777645, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of propane-1,2-diol (4.00 g, 52.0 mmol) in dry dichloromethane (50 mL) at 0° C. was added trityl chloride (15 g, 0.052 mol), N,N-dimethylaminopyridine (0.82 g, 6.8 mmol) and triethylamine (13.13 g, 1.33 mmol). The resulting mixture was stirred at room temperature for 14 hours. Methanesulfonyl chloride (6.36 g, 56.0 mmol) slowly at 0° C. Then the reaction was stirred at room temperature for 2 hours. The reaction mixture was diluted with water (100 mL) and extracted with dichloromethane (100 mL*3). The organic layer was washed with water (100 mL), and 1N hydrochloric acid (100 mL*2). The combined organic layers were dried over sodium sulfate and concentrated to give a crude product, which was purified on silica gel column (petroleum ether:ethyl acetate=8:1 to 10:1) to give the title compound (15 g) as a viscous oil, which was used in the next step without further purification.

Workup

  1. customslowly at 0° C
  2. stirringThen the reaction was stirred at room temperature for 2 hours
  3. extractionextracted with dichloromethane (100 mL*3)
  4. washThe organic layer was washed with water (100 mL), and 1N hydrochloric acid (100 mL*2)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated
  7. customto give a crude product, which
  8. customwas purified on silica gel column (petroleum ether:ethyl acetate=8:1 to 10:1)

Sources & evidence

ORD record
ord-670c8e7f86944c508298d264716aaa65
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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