Sodium hydride → HCID 11356093, compound

HRID 1180778Notes

Reaction equation

HRID 1180778 reaction equation
[OH:1][CH2:2][C:3]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4]1.[H-].[Na+].Br[C:12]1[S:13][CH:14]=[CH:15][N:16]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O.O1CCCC1.C(OCC)(=O)C>[S:13]1[CH:14]=[CH:15][N:16]=[C:12]1[O:1][CH2:2][C:3]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 764302-BromothiazoleHCID 516892Sodium BicarbonateHCID 4498243Cyclobutane-1,1-diyldimethanol

Product 1

HCID 11356093HCID 11356093, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a solution of 0.5 g (4.31 mmol) of [1-(hydroxymethyl)cyclobutyl]methanol in 15 mL of N,N-dimethylformamide:tetrahydrofuran (1:1), was added a 60% dispersion of 0.165 g (4.31 mmol) sodium hydride in oil. After stirring for 15 min, 0.71 g (4.31 mmol) of 2-bromothiazole was added and the contents refluxed for 3 h. A saturated solution of sodium bicarbonate was added followed by ethyl acetate. The organic phase was isolated, dried with magnesium sulfate and concentrated under vacuum. The crude product was purified by silica gel chromatography eluting with ethyl acetate:hexane (4:6) to afford 0.340 g (40%) of {1-[(1,3-thiazol-2-yloxy)methyl]cyclobutyl}methanol as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.05 (d, J=4 Hz, 1H), 6.64 (d, J=4 Hz, 1H), 4.51 (s, 2H), 3.59 (s, 2H), 2.03-1.72 (m, 6H). GC-MS m/z 200 (M+H).

Workup

  1. temperaturethe contents refluxed for 3 h
  2. customThe organic phase was isolated
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe crude product was purified by silica gel chromatography
  6. washeluting with ethyl acetate:hexane (4:6)

Sources & evidence

ORD record
ord-882af5ceed6a42cabc995e15f7388b88
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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