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Triethylamine → methanesulfonic acid Trans-2-benzhydryl-tetrahydropyran-4-yl ester

HRID 1429006
Notes
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Reaction equation

HRID 1429006 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH:6]([C@H:19]1[CH2:24][C@H:23]([OH:25])[CH2:22][CH2:21][O: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>C(Cl)Cl>[CH:6]([C@H:19]1[CH2:24][C@H:23]([O:25][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:22][CH2:21][O:20]1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66631792trans-2-Benzhydryl-tetrahydropyran-4-ol

Product 1

HCID 86605343methanesulfonic acid Trans-2-benzhydryl-tetrahydropyran-4-yl esterYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (0.62 g, 5.41 mmol) in dry methylene chloride (10 ml) was added dropwise to a mixture of trans-2-diphenylmethyl-4-hydroxypyran 3a (0.73 g, 2.70 mmol), triethylamine (0.41 g, 4.06 mmol) in methylene chloride (10 ml) and was cooled to 0° C. After one hour, the reaction was gradually allowed to reach room temperature over a period of four hours. Additional methylene chloride (20 ml) was added to the reaction mixture, and the mixture was washed in turn with saturated aqueous sodium bicarbonate, brine and water, then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and purification by flash chromatography gave compound 4a (0.93 g, 99.9% yield) as an oil.

Workup

  1. waitto reach room temperature over a period of four hours
  2. washthe mixture was washed in turn with saturated aqueous sodium bicarbonate, brine and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure, and purification by flash chromatography

Sources & evidence

ORD record
ord-f0a14f66a73e477381d41718e106d35c
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08937189B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes