Water → 4,4-Dimethyl-2-(4'-methanesulfonyloxymethylbipbenyl-2-yl)oxazoline

HRID 53430

Reaction equation

HRID 53430 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][OH:20])=[CH:15][CH:14]=2)=[N:3]1.C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31].O>C(Cl)Cl>[CH3:1][C:2]1([CH3:21])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:14]=[CH:15][C:16]([CH2:19][O:20][S:30]([CH3:29])(=[O:32])=[O:31])=[CH:17][CH:18]=2)=[N:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 110658764,4-Dimethyl-2-(4'hydroxymethylbiphenyl-2-yl)oxazoline

Product 1

HCID 153808784,4-Dimethyl-2-(4'-methanesulfonyloxymethylbipbenyl-2-yl)oxazolineYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.0 g (7.1 mmol) of 4,4-dimethyl-2-(4'-hydroxymethylbiphenyl-2-yl)oxazoline and 1.43 g (14.1 mmol) of triethylamine were dissolved in methylene chloride (20 ml). A solution of 0.98 g (8.6 mmol) of methanesulfonyl chloride in methylene chloride (10 ml) was dropwise added thereto under cooling with salt-ice. After stirring for 8 hours as such, the reaction liquid was poured into water, followed by the extraction with methylene chloride. After washing with water and drying, vacuum concentration was conducted. 2.53 g of the title compound was obtained as an oil (yield 99%).

Workup

  1. customthe reaction liquid
  2. extractionfollowed by the extraction with methylene chloride
  3. washAfter washing with water
  4. customdrying
  5. concentrationvacuum concentration

Sources & evidence

ORD record
ord-7c9204b934f345e6aa8ab56122a191e0
Source dataset
uspto-grants-1997_04
Patent number
US05618969

Linked notes

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