Dichloromethane → 3-Methoxy-3-(4-phenylphenyl)but-1-yl p-toluenesulfonate

HRID 1065991Notes

Reaction equation

HRID 1065991 reaction equation
[CH3:1][O:2][C:3]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)([CH3:7])[CH2:4][CH2:5][OH:6].C(N(CC)CC)C.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.ClCCl>CC(C)=O.C(OCC)C>[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33]([O:6][CH2:5][CH2:4][C:3]([O:2][CH3:1])([C:8]2[CH:9]=[CH:10][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][CH:13]=2)[CH3:7])(=[O:35])=[O:34])=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 154045023-Methoxy-3-(4-phenylphenyl)butan-1-ol

Product 1

HCID 537569453-Methoxy-3-(4-phenylphenyl)but-1-yl p-toluenesulfonateYield 87.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-methoxy-3-(4-phenylphenyl)butan-1-ol (2.04 g, 8.0 mmole, prepared in Example 8, Part B above) and triethylamine (1.51 g, 15 mmole) in acetone (10 mL) at 0° was added in one portion a solution of p-toluenesulfonyl chloride (2.85 g, 15 mmole) in acetone (4 mL). The resultant suspension was warmed to 20° C. and stirred at that temperature for 14 hours, then diluted with diethyl ether (40 mL). The resultant precipitate (triethylamine hydrochloride) was removed by filtration and the filtrate was evaporated to dryness to give a crude product, which was purified by column chromatography on silica gel, eluting with a 1:1 v/v hexanes:dichloromethane mixture to give the desired product (2.87 g, 87% yield) of colorless solid. Less pure fractions were combined to provide an additional 0.147 g of colorless solid which was crystallized from hexanes (10 mL), furnishing colorless fine matted needles weighing 0.070 g; melting point 69-70.5° C.

Workup

  1. customThe resultant precipitate (triethylamine hydrochloride) was removed by filtration
  2. customthe filtrate was evaporated to dryness
  3. customto give a crude product, which
  4. customwas purified by column chromatography on silica gel
  5. washeluting with a 1:1 v/v hexanes

Sources & evidence

ORD record
ord-0cb72041fc284773a2497113dc75be5c
Source dataset
uspto-grants-2001_06
Patent number
US06242154B1

Reaction notes

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