Imidazole → HCID 68970576, compound

HRID 456000Notes

Reaction equation

HRID 456000 reaction equation
[OH:1][CH:2]1[CH:8]([OH:9])[C:7]2([CH3:11])[O:10][C:3]1([CH3:13])[CH2:4][C:5](=[O:12])[CH2:6]2.N1C=CN=C1.[C:19]([Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])(Cl)Cl)([CH3:22])([CH3:21])[CH3:20]>ClCCCl>[C:19]([Si:23]1([C:26]([CH3:29])([CH3:28])[CH3:27])[O:1][CH:2]2[CH:8]([C:7]3([CH3:11])[O:10][C:3]2([CH3:13])[CH2:4][C:5](=[O:12])[CH2:6]3)[O:9]1)([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 87624Silane, dichlorobis(1,1-dimethylethyl)-HCID 68732637HCID 68732637, compound

Product 1

HCID 68970576HCID 68970576, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 6,7-dihydroxy-1,5-dimethyl-8-oxa-bicyclo[3.2.1]octan-3-one (Bulletin of the Chemical Society of Japan (1983), 56(9), 2680-99, 550 mg, 2.95 mmol) in DCE (20 mL) was added imidazole (2.0 g, 29 mmol) and di-tert-butyldichlorosilane (1.2 mL, 5.9 mmol). The resulting mixture was stirred under Ar for 48 h. The reaction mixture was treated with satd. NaHCO3 (20 mL) and the DCE layer was separated, dried (Na2SO4) and concentrated and the residue obtained was purified on silica gel (5-20% EtOAc/hexane) to obtain the title compound (869 mg, 90%). 1H-NMR (CDCl3; 400 MHz): δ 4.23 (s, 2H), 2.43 (d, 1H, J=15.6 Hz), 2.31 (d, 1H, J=15.6 Hz), 1.45 (s, 6H), 1.12 (s, 9H), 1.04 (s, 9H).

Workup

  1. additionThe reaction mixture was treated with satd
  2. customNaHCO3 (20 mL) and the DCE layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customthe residue obtained
  6. customwas purified on silica gel (5-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-c47956d9ba5d4246bc38b21c9306186d
Source dataset
uspto-grants-2013_07
Patent number
US08497376B2

Reaction notes

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