Imidazole → HCID 68771119, compound

HRID 2265234Notes

Reaction equation

HRID 2265234 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([CH3:14])[C@@H:10]([OH:13])[CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[Cl:8].N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C(Cl)Cl>[C:23]([Si:20]([CH3:22])([CH3:21])[O:12][CH2:11][C@H:10]([OH:13])[C@@H:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH3:14])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 68773669HCID 68773669, compound

Product 1

HCID 68771119HCID 68771119, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2R,3R)-3-(3,4-dichloro-phenyl)-butane-1,2-diol (3.20 g, 13.6 mmol) and imidazole (1.39 g, 20.4 mmol) in DCM (28 mL) at rt was added tert-butyldimethylsilyl chloride (TBSCl; 2.15 g, 14.3 mmol). The solution was stirred for 1 h then quenched by addition of satd. aq. NH4Cl (100 mL). The mixture was stirred for 5 min, the layers were separated, and the aqueous layer was extracted with DCM (3×). The combined organic layers were dried (Na2SO4) and concentrated to yield a viscous yellow liquid. The product was purified by flash chromatography (EtOAc/hexanes) to afford 4.52 g (95%) of the desired product as a colorless viscous liquid. 1H NMR (400 MHz, CDCl3): 7.37 (d, J=8.3, 1H), 7.36 (d, J=2.1, 1H), 7.10 (dd, J=8.2, 2.1, 1H), 3.75-3.68 (m, 1H), 3.65 (dd, J=9.9, 3.8, 1H), 3.45 (dd, J=9.9, 7.1, 1H), 2.81 (quint, J=7.0, 1H), 2.37 (d, J=4.0, 1H), 1.25 (d, J=7.2, 3H), 0.89 (s, 9H), 0.07 (s, 3H), 0.06 (s, 3H).

Workup

  1. customthen quenched by addition of satd
  2. stirringThe mixture was stirred for 5 min
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted with DCM (3×)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated
  7. customto yield a viscous yellow liquid
  8. customThe product was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-fd0af10d9d66420c97060d464da0c97f
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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