2-(Tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-4-ol → 2-(tert-Butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran4-one

HRID 1594824Notes

Reaction equation

HRID 1594824 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:16])([CH3:15])[CH:8]1[CH2:13][CH:12]([OH:14])[CH2:11][CH2:10][O:9]1)([CH3:4])([CH3:3])[CH3:2]>CS(C)=O.CCN(CC)CC>[C:1]([SiH2:5][O:6][C:7]([CH3:16])([CH3:15])[CH:8]1[CH2:13][C:12](=[O:14])[CH2:11][CH2:10][O:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 1317228412-(Tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-4-ol

Product 1

HCID 1317228402-(tert-Butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran4-oneYield 66%

Reagents, catalysts & solvents 1

HCID 86583882DMSO triethylamineSolvent

Procedure

A solution of 2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-4-ol (2.27 g, 9.21 mmol) in anhydrous DMSO/Et3N (15/13 mL) was treated with sulfur trioxide pyridine complex (7.33 g, 46.1 mmol) portionwise at room temperature. After stirring for 1 hour, the reaction was concentrated and the residue was partitioned between EtOAc (100 mL) and water (50 ml). The separated organic layer was washed with brine (70 mL), dried over sodium sulfate, and concentrated. Purification by silica gel column using 10-20% of EtOAc in hexane afforded 1.48 g (66%) of colorless oil: 1H NMR (CDCl3) δ 0.05 (s, 6H), 0.88 (s, 9H), 2.32 (dt, 1H), 2.41 (m, 2H), 2.58 (m, 1H), 3.62 (m, 2H), 3.70 (d, 2H), 4.31 (m, 1H).

Workup

  1. concentrationthe reaction was concentrated
  2. customthe residue was partitioned between EtOAc (100 mL) and water (50 ml)
  3. washThe separated organic layer was washed with brine (70 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification by silica gel column

Sources & evidence

ORD record
ord-b626d4b580404e96bd49b7757ed1c3e8
Source dataset
uspto-grants-2001_09
Patent number
US06284764B1

Reaction notes

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