Sodium;3-oxidodioxaborirane;tetrahydrate → (1,1-Dioxo-hexahydro-1lambda6-thiopyran-4-yl)-pyridin-2-yl-methanol

HRID 1806087Notes

Reaction equation

HRID 1806087 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([CH:9]1[CH2:14][CH2:13][S:12][CH2:11][CH2:10]1)[OH:8].B1([O-])OO1.[OH2:19].[OH2:20].O.O.[Na+]>C(O)(=O)C>[O:19]=[S:12]1(=[O:20])[CH2:11][CH2:10][CH:9]([CH:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[OH:8])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrateHCID 66995230pyridin-2-yl(tetrahydro-2H-thiopyran-4-yl)methanol

Product 1

HCID 66995296(1,1-Dioxo-hexahydro-1lambda6-thiopyran-4-yl)-pyridin-2-yl-methanolYield 68.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Placed pyridin-2-yl(tetrahydro-2H-thiopyran-4-yl)methanol (1.560 g, 7.453 mmol) in glacial acetic acid (2 mL). Sodium perborate tetrahydrate (2.293 g, 14.91 mmol) was added and stirred for 18 hours. The reaction was partitioned between saturated sodium bisulfite and CH2Cl2. The solids were filtered off, washed with water and dried to afford the title compound (1.233 g, 68.56% yield)

Workup

  1. customThe reaction was partitioned between saturated sodium bisulfite and CH2Cl2
  2. filtrationThe solids were filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-72cabc3c7b2341a2a80c20c10a52c624
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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