Potassium Carbonate → 2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-ethynyl-tetrahydro-pyran4-ol

HRID 1264045Notes

Reaction equation

HRID 1264045 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:22])([CH3:21])[CH:8]1[CH2:13][C:12]([C:15]#[C:16][Si](C)(C)C)([OH:14])[CH2:11][CH2:10][O:9]1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+]>>[C:1]([SiH2:5][O:6][C:7]([CH3:22])([CH3:21])[CH:8]1[CH2:13][C:12]([C:15]#[CH:16])([OH:14])[CH2:11][CH2:10][O:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 11430Potassium CarbonateHCID 1317228422-(tert-Butyl-dimethyl-silanyloxymethyl)-4-trimethylsilanylethynyltetrahydro-pyran-4-ol

Product 1

HCID 1317238332-(tert-Butyl-dimethyl-silanyloxymethyl)-4-ethynyl-tetrahydro-pyran4-ol

Procedure

A mixture of 2-(tert-butyl-dimethyl-silanyloxymethyl)-4-trimethylsilanylethynyl-tetrahydro-pyran-4-ol (1.75 g, 5.1 mmol) and K2CO3 (1.4 g, 10.2 mmol) was stirred at room temperature for 30 minutes. After concentration, the residue was partitioned between EtOAc (50 mL) and water (30 mL) and the separated aqueous layer was extracted with EtOAc. The combined organic extract was dried over sodium sulfate and concentrated to give 1.33 g (96%) of light yellow oil: 1H NMR (CDCl3) δ 0.05 (s, 6H), 0.88 (s, 9H), 1.50 (m, 1H), 1.78 (m, 1H), 1.84 (d, 1H), 2.01 (m, 1H), 2.55 (s, 1H), 3.55-3.70 (m, 4H), 4.00 (m, 1H).

Workup

  1. concentrationAfter concentration
  2. customthe residue was partitioned between EtOAc (50 mL) and water (30 mL)
  3. extractionthe separated aqueous layer was extracted with EtOAc
  4. extractionThe combined organic extract
  5. dry with materialwas dried over sodium sulfate
  6. concentrationconcentrated
  7. customto give 1.33 g (96%) of light yellow oil

Sources & evidence

ORD record
ord-2289a1af696e4ad8bfb006b343f0eeed
Source dataset
uspto-grants-2003_04
Patent number
US06541481B2

Reaction notes

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