Triethylamine → Methanesulfonic acid trans-6-benzhydryl-tetra-hydropyran-3-yl ester

HRID 78898Notes

Reaction equation

HRID 78898 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH:6]([C@@H:19]1[O:24][CH2:23][C@@H:22]([OH:25])[CH2:21][CH2:20]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[O:24][CH2:23][C@@H:22]([O:25][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:21][CH2:20]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

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11608697Trans-6-benzhydryl-tetrahydropyran-3-ol

Product 1

HCID 11566406Methanesulfonic acid trans-6-benzhydryl-tetra-hydropyran-3-yl esterYield 78.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.33 g, 2.87 mmol) was reacted with trans-2-diphenylmethyl-tetrahydropyran-5-ol 11 (0.38 g, 1.43 mmol) in the presence of triethylamine (0.22 g, 2.15 mmol) in methylene chloride (10 ml) to give trans-2-diphenylmethyl-tetrahydropyran-5-yl methanesulfonate 13 (0.39 g, 77.8%) as an oil (Procedure A).

Sources & evidence

ORD record
ord-cfb441500b69483292f527e6d6d7ec12
Source dataset
uspto-grants-2014_09
Patent number
US08841464B2

Reaction notes

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