Imidazole → 2-[(tert-Butyldimethylsilyl)oxymethyl]-6-chlorobenzyl alcohol

HRID 1766928Notes

Reaction equation

HRID 1766928 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][OH:9])[C:3]=1[CH2:10][OH:11].N1C=CN=C1.[C:17]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])([CH3:19])[CH3:18].O>O1CCCC1.CCCCCC.C(OCC)(=O)C>[Si:21]([O:9][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH2:10][OH:11])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:23])[CH3:22]

Participants

8

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 17862674(3-Chloro-1,2-phenylene)dimethanol

Product 1

HCID 468330572-[(tert-Butyldimethylsilyl)oxymethyl]-6-chlorobenzyl alcoholYield 73.5%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-chloro-1,2-benzenedimethanol (described in J. Chem. Soc., p. 5050 (1952); 3.02 g, 17.5 mmol) in tetrahydrofuran (40 ml) was cooled to 0° C., and then imidazole (1.19 g, 17.5 mmol) and tert-butylchlorodimethylsilane (2.64 g, 17.5 mmol) were added thereto. The mixture was stirred at room temperature for 1 hour, then water was added thereto, and the product was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and the solvent was distilled off under reduced pressure to give a residue. The residue was subjected to chromatography on a silica gel (100 g) column (eluent; ethyl acetate:hexane=1:5) to afford the title compound (3.69 g, 73% yield) as a colorless oil.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. distillationthe solvent was distilled off under reduced pressure
  4. customto give a residue

Sources & evidence

ORD record
ord-03f0c4e3b5bf4639b21995133ab020fe
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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