Methanesulfonyl chloride → HCID 86610159, compound

HRID 1363213Notes

Reaction equation

HRID 1363213 reaction equation
[C:1]1([C@H:7]2[CH2:12][C@@H:11]([OH:13])[CH2:10][CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[CH3:23][S:24]([O:13][C@H:11]1[CH2:10][CH2:9][O:8][C@@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:12]1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 11423901cis-2-phenyltetrahydro-2H-pyran-4-ol

Product 1

HCID 86610159HCID 86610159, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of cis-2-phenyltetrahydro-2H-pyran-4-ol (1 g) in DCM (20 mL) was cooled in an ice-salt water bath and treated with DIEA (2.2 g) and methanesulfonyl chloride (0.7 g) for 2 hours. The mixture was diluted with DCM (50 mL) and washed with water and brine. The organic layer was dried and concentrated. Preparative TLC provided 0.9 g of cis-2-phenyl-tetrahydro-2H-pyran-4-yl methanesulfonate.

Workup

  1. washwashed with water and brine
  2. customThe organic layer was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8d10b390854d49fe90b5c7f587dbb0c7
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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