Imidazole → HCID 68856971, compound

HRID 226110Notes

Reaction equation

HRID 226110 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C@@H:11]([OH:13])[CH3:12])[C:5]=2[O:4][C:3]=1[CH3:14].N1C=CN=C1.[CH3:20][C:21]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])[CH3:22]>C(Cl)Cl>[Br:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C@@H:11]([O:13][Si:24]([C:21]([CH3:23])([CH3:22])[CH3:20])([CH3:26])[CH3:25])[CH3:12])[C:5]=2[O:4][C:3]=1[CH3:14]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 68858182HCID 68858182, compound

Product 1

HCID 68856971HCID 68856971, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (S)-1-(3-bromo-2-methyl-benzofuran-7-yl)-ethanol (1.39 g, 5.47 mmol) in CH2Cl2 (50 mL) is treated with imidazol (0.56 g, 8.21 mmol) and TBSCl (0.91 g, 6.02 mmol). The reaction is stirred at rt overnight. It is diluted with CH2Cl2 (50 mL); washed with 0.1 M HCl (3×30 mL); dried with Na2SO4; filtered and concentrated. The resulting crude material is purified by chromatography gives the title compound (1.92 g, 5.19 mmol, 95%). 1H NMR (CDCl3): δ. −0.02 (s, 3H), 0.07 (s, 3H), 0.91 (s, 3H), 2.48 (s, 3H), 1.52 (d, J=6.2 Hz, 3H), 5.38 (q, J=6.2 Hz, 1H), 7.25 (t, J=8.0 Hz, 1H), 7.30 (dd, J=8.0, 1.7 Hz, 1H), 7.40 (d, J=8.0 Hz, 1H) ppm.

Workup

  1. washwashed with 0.1 M HCl (3×30 mL)
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting crude material is purified by chromatography

Sources & evidence

ORD record
ord-8e021bfd5b884ab2b79b811375fd3869
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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