Imidazole → HCID 69198304, compound

HRID 2118300Notes

Reaction equation

HRID 2118300 reaction equation
[CH2:1]([Si:3](Cl)([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[Br:9][CH2:10][C@@H:11]([C:13]1[CH:24]=[CH:23][C:16]2[O:17][C:18]([CH3:22])([CH3:21])[O:19][CH2:20][C:15]=2[CH:14]=1)[OH:12].N1C=CN=C1>CN(C=O)C>[Br:9][CH2:10][C@H:11]([O:12][Si:3]([CH2:6][CH3:7])([CH2:4][CH3:5])[CH2:1][CH3:2])[C:13]1[CH:24]=[CH:23][C:16]2[O:17][C:18]([CH3:22])([CH3:21])[O:19][CH2:20][C:15]=2[CH:14]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 25098927(R)-2-Bromo-1-(2,2-dimethyl4H-benzo[1,3]dioxin-6-yl)ethanol

Product 1

HCID 69198304HCID 69198304, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
15 °C

Procedure

Triethylsilyl chloride (205 g) was added dropwise to a stirred mixture of (1R)-2-Bromo-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (350 g) and imidazole (108.5 g) in DMF (875 ml) at 5° C. Upon complete addition the mixture was warmed to 15° C. and stirred, at this temperature for 1 h. N-hexane (3500 ml) was then added to the mixture which was washed with water (3×1750 ml). The organic layer was dried over anhydrous MgSO4 before being filtered and concentrated under reduced pressure to give the title compound (488.6 g) as an oil, LC RT=7.97 min, δ (DMSO-d6) 7.18 (1H, d, J 8.2 Hz), 7.10 (1H, s), 6.75 (1H, d, J 8.2 Hz), 4.83 (1H, m), 4.78 (2H, d, J 6.9 Hz), 3.55 (2H, m), 1.45 (6H, s), 0.84 (9H, t, J 8.1 Hz), 0.51 (6H, m).

Workup

  1. additionUpon complete addition the mixture
  2. washwas washed with water (3×1750 ml)
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationbefore being filtered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c5b7eeb8ab804c928bafb334bb095863
Source dataset
uspto-grants-2008_10
Patent number
US07442837B2

Reaction notes

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