Tetrahydro-4H-pyran-4-ol → HCID 68182400, compound

HRID 524392Notes

Reaction equation

HRID 524392 reaction equation
[N+](=[C:3]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:4]([O:6][CH3:7])=[O:5])=[N-].[OH:23][CH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>C(Cl)Cl.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[O:27]1[CH2:28][CH2:29][CH:24]([O:23][CH:3]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)(=[O:16])=[O:15])=[CH:10][CH:9]=2)[C:4]([O:6][CH3:7])=[O:5])[CH2:25][CH2:26]1

Participants

5

Reactant 2

HCID 74956Tetrahydro-4H-pyran-4-olHCID 86669538HCID 86669538, compound

Product 1

HCID 68182400HCID 68182400, compoundYield 83.4%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
25 °C

Procedure

Methyl 2-diazo-2-(4-tetrahydropyran-4-ylsulfonylphenyl)acetate (4.0 g, 12.34 mmol) was dissolved in DCM (40 mL) under argon atmosphere. To this solution, 4-hydroxy tetrahydropyran (1.5 g, 14.8 mmol) was added followed by rhodium (II) acetate dimer (0.109 g, 0.24 mmol). Mixture was stirred at 25° C. for 30 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 as methyl 2-tetrahydropyran-4-yloxy-2-(4-tetrahydropyran-4-ylsulfonylphenyl)acetate (4.1 g).

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-f05c17e3448a4328a9e6e2a502d01ffe
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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