Triethylamine → HCID 17954496, compound

HRID 747226Notes

Reaction equation

HRID 747226 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH:11]([CH2:13][OH:14])[O:10][N:9]=2)=[CH:4][C:3]=1[F:15].C(N(CC)CC)C.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>ClCCl.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH:11]([CH2:13][O:14][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[O:10][N:9]=2)=[CH:4][C:3]=1[F:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 17954502HCID 17954502, compound

Product 1

HCID 17954496HCID 17954496, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

[3-(4-Bromo-3-fluorophenyl)-4,5-dihydroisoxazol-5-yl]methanol (7.518 g, 27.4 mmol) was dissolved in a mixture of triethylamine (4.59 ml, 33.0 mmol) and dichloromethane (100 ml). The resulting solution was cooled to 0° C., then a 1M solution of tert-butyldimethylsilylchloride (30.2 ml) in dichloromethane was added dropwise over 30 minutes. 4-Dimethylamino pyridine (0.67 g, 5.48 mmol) was added and the reaction mixture left to stir overnight at room temperature. The reaction mixture was washed with water (200 ml). The dichloromethane layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo to yield 9.263 g (87%) of the desired compound as a colourless oil.

Workup

  1. waitthe reaction mixture left
  2. washThe reaction mixture was washed with water (200 ml)
  3. customThe dichloromethane layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7db7bbe5ea104be38c73a6fb2efa4a77
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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