Water → 3-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-5-methylisoxazole

HRID 128759Notes

Reaction equation

HRID 128759 reaction equation
[OH:1][CH2:2][C:3]1[CH:7]=[C:6]([CH3:8])[O:5][N:4]=1.[Si:9](Cl)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].C(N(CC)CC)C.O>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Si:9]([O:1][CH2:2][C:3]1[CH:7]=[C:6]([CH3:8])[O:5][N:4]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 2736567(5-Methyl-1,2-oxazol-3-yl)methanol

Product 1

HCID 100139813-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-5-methylisoxazoleYield 82.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a chilled (5° C.) solution of 3-hydroxymethyl -5-methylisoxazole (16.8 g, 148 mmol) and tert-butyldimethylsilyl chloride (24.6 g, 163 mmol) in dry methylene chloride (100 mL) was added over 15 minutes a solution of triethylamine (22.7 mL, 163 mmol) in methylene chloride (25 mL). 4-Dimethylaminopyridine (1.81 g, 14.8 mmol) was added and the thick reaction mixture was stirred at room temperature for 48 hours. Water (100 mL) was added and the aqueous layer extracted with methylene chloride (3x). The combined organic phases were washed with brine, dried (MgSO4), filtered through a pad composed of a layer of Florisil and a layer of Silica Gel 60, and concentrated in vacuo. The yellow oil obtained (36.6 g) was purified by chromatography (Silica Gel 60, 2% ethyl acetate in hexanes) to give 27.7 g (81.9%) of pure title compound as a pale yellow oil.

Workup

  1. extractionthe aqueous layer extracted with methylene chloride (3x)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered through a pad
  5. concentrationa layer of Silica Gel 60, and concentrated in vacuo
  6. customThe yellow oil obtained (36.6 g)
  7. customwas purified by chromatography (Silica Gel 60, 2% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-268fd64174f44cb1a21982bd9a2bc3e4
Source dataset
uspto-grants-1995_11
Patent number
US05464848

Reaction notes

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