Tetrahydro-4H-pyran-4-ol → HCID 68182653, compound

HRID 524395Notes

Reaction equation

HRID 524395 reaction equation
[CH:1]1([S:6]([C:9]2[N:14]=[CH:13][C:12]([C:15](=[N+]=[N-])[C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=2)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:22][CH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>C(Cl)Cl.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH:1]1([S:6]([C:9]2[N:14]=[CH:13][C:12]([CH:15]([O:22][CH:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=2)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 74956Tetrahydro-4H-pyran-4-olHCID 86669540HCID 86669540, compound

Product 1

HCID 68182653HCID 68182653, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

Methyl 2-(6-cyclopentylsulfonyl-3-pyridyl)-2-diazo-acetate (0.25 g, 0.80 mmol) was dissolved in DCM (5 mL) under argon atmosphere. To this solution, 4-hydroxy tetrahydropyran (0.11 mL, 1.21 mmol) was added followed by rhodium (II) acetate dimer (9 mg, 0.021 mmol). Mixture was stirred at 25° C. for 60 min. Reaction mixture was diluted with DCM (10 mL), organic layer was washed with water followed by brine solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a crude product (280 mg).

Workup

  1. customReaction mixture
  2. washwas washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dba90d0a47ed4bbbbf3d217c8e732dbd
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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